Nucleus Mar 2014

20
March 2014 Vol. XCII, No. 7 N O R T H E A S T E R N S E C T I O N A M E R I C A N C H E M I C A L S O C I E T Y F O U N D E D 1 8 9 8 N E S A C S Monthly Meeting 2013 Nobel Laureate Martin Karplus to speak at the Boston/Cambridge Courtyard Marriott Summer Scholar Report By Kyle Murphy and Edward J. Brush, Bridgewater State University Chem Camp from the Other Side By Jacob Sanders Norris Award Symposium Monday, March 17, 2014 at Omni Dallas Hotel

description

Featured speaker at March 6, 2014 NESACS meeting is 2013 Nobel Prize winner, Professor Emeritus, Martin Karplus of Harvard University.

Transcript of Nucleus Mar 2014

http://www.nesacs.org

March 2014 Vol. XCII, No. 7

NORTHEASTERN SECTION • AMERICAN CHEMIC

ALSO

CIET

Y

FOUNDED 1898

NESACS

Monthly Meeting2013 Nobel Laureate Martin Karplus to speak at theBoston/Cambridge Courtyard Marriott

Summer Scholar ReportBy Kyle Murphy and Edward J. Brush, BridgewaterState University

Chem Camp fromthe Other SideBy Jacob Sanders

Norris AwardSymposiumMonday, March 17, 2014 at Omni Dallas Hotel

2 The Nucleus March 2014

This past June, I had the opportu-nity to serve as the Peer Mentor at theUS National Chemistry Olympiad(USNCO) Study Camp, held at the USAir Force Academy in ColoradoSprings. The program, colloquiallyreferred to as “Chem Camp,” bringstogether the top 20 high-school chem-istry students across the entire country(based on the national selection exam)to prepare them for the InternationalChemistry Olympiad.

For two weeks, the students dedi-cate themselves to chemistry: theyattend advanced theoretical lectures onorganic, inorganic, physical, analytical,and biochemistry; they work with thementors and with each other to solvechallenging problems in all of thesefields; and they work in the laboratoryevery afternoon to master advancedtechniques. At the end, the top fourstudents, along with two alternates, areselected to represent the United Statesat the International ChemistryOlympiad, which comprises a five-hour theoretical exam and a five-hourlaboratory practical exam.

As a high school student, Iattended Chem Camp in June 2005,where I was selected to attend the 37th

International Chemistry Olympiad inTaipei, Taiwan. The entire experience,from the study camp to the interna-tional exam, was such a formative onethat I jumped at the opportunity toreturn this year to the study camp asthe Peer Mentor. This article is mybehind-the-scenes look at Chem Campfrom the “other” side—that of thementors and instructors.

Preparation for the study campbegins long before June. In January,the host country of the upcoming inter-national exam releases a book ofPreparatory Problems: about 30 theo-retical problems and 10 laboratoryexperiments. The problems are reallyflippin’ hard, creatively combiningmany advanced topics into a singlequestion, and they define the scope ofthe international competition by indi-cating which topics will be empha-

sized. Since the competition this pastyear was hosted by Russia, a countrywith a long olympiad tradition, theproblems were even harder thanusual—many at the level of a graduatestudent!

My first task as Peer Mentor—long before the camp started—was towork through the theoretical problems.Some took many hours; othersrequired that I learn topics far afieldfrom my expertise (for me, the realzingers are inorganic chemistry!). Thechemistry nerd in me loved thisprocess—I got to confront topics I had-n’t thought about in a long time. Iknew it was important to understandevery problem inside-out, as I wouldsoon face 20 bright students askinghard detail-oriented questions. In addi-tion, I searched for other problems—mostly from old olympiadexams—covering similar concepts.These could be used as practice prob-lems or exam questions.

Armed with a large binder full ofmy notes and solutions to the Prepara-tory Problems, I arrived at the US AirForce Academy with the three mentorsthree days before the students. Thosethree days went by in a blur: coordinat-

ing with lecturers, buying supplies,and—most importantly—setting uplaboratory stations and making sure allthe experiments were ready to go. Thementors took the lead in this enormoustask: prior to the camp, they tested allthe laboratory experiments in thePreparatory Problems and designedadditional experiments to give the stu-dents practice with the techniquesbeing emphasized by the Russians.Their dedication to designing, tweak-ing, and managing so many compli-cated experiments is the main reasonour team performs so strongly on thepractical component of the interna-tional exam. The three days of prepa-ration flew by and, before we knew it,the students started to arrive.

Meeting the students for the firsttime is an inspiring experience. Onestudent, barely after putting down hisluggage, started to ask me deep andsophisticated questions about advancedequilibrium techniques—a topic I wasscheduled to lecture later in the camp.(I silently noted that I needed to makemy lecture harder and more advanced.)But most important is the camaraderiethat emerges when you bring 20 stu-dents obsessed with chemistry—for thefirst time—in the same place. One ofthe most memorable moments is theopening dinner, where the studentsreceive six college-level textbooksranging across all the subfields ofchemistry. You can see the look ofChristmas-come-early in some of theireyes—see the picture if you don’tbelieve me!

Chem Camp from the Other SideJacob Sanders is a Ph.D. Candidate in Chemical Physics and Head Teaching Fellow at Harvard University.

continued o n page 4

From student (June 2005, top left) to mentor(June 2013, bottom)

Christmas in June! The students receive theirtextbooks.

The Nucleus March 2014 3

The Nucleus is published monthly, except June and August, by the Northeastern Section of the AmericanChemical Society, Inc. Forms close for advertising on the 1st of the month of the preceding issue. Textmust be received by the editor six weeks before the date of issue.Editor: Michael P. Filosa, Ph.D., 18 Tamarack Road, Medfield, MA 02052 Email:

filosam(at)verizon.net; Tel: 508-843-9070Associate Editors: Myron S. Simon, 60 Seminary Ave. apt 272, Auburndale, MA 02466,

Mindy Levine, 516-697-9688, mindy.levine(at)gmail.comBoard of Publications: James Phillips (Chair), Vivian K. Walworth, Mary Mahaney Business Manager: Karen Piper, 19 Mill Rd., Harvard, MA 01451, Tel: 978-456-8622Advertising Manager: Vincent J. Gale, P.O. Box 1150, Marshfield, MA 02050,

Email: Manager-vincegale(at)mboservices.net; Tel: 781-837-0424Contributing Editors: Morton Hoffman, Feature Editor; Dennis Sardella, Book Reviews Calendar Coordinator: Xavier Herault, Email: xherault(at)netzero.netPhotographers: Morton Hoffman and James PhillipsProofreaders: Donald O. Rickter, Vivian K. Walworth, Mindy Levine Webmaster: Roy HagenCopyright 2014, Northeastern Section of the American Chemical Society, Inc.

The Northeastern Section of the AmericanChemical Society, Inc.Office: Anna Singer, 12 Corcoran Road,Burlington, MA 01803(Voice or FAX) 781-272-1966.e-mail: secretary(at)nesacs.orgNESACS Homepage:http://www.NESACS.orgOfficers 2014ChairCatherine CostelloBoston University School of Medicine670 Albany Street, room 511Boston, MA 02118-2646Cecmsms(at)bu.eduChair-ElectKatherine L. LeePfizer200 CambridgePark Drive, t6014KCambridge, MA 02140katherine.lee(at)pfizer.com617-665-5664Immediate Past ChairLiming Shao158 South Great RoadLincoln, MA 01773Shao(at)fas.harvard.edu781-518-0720Secretary:Michael SingerSigma-Aldrich3 Strathmore Rd, Natick, MA 01360774-290-1391, michael.singer(at)sial.comTreasurer:James Piper19 Mill Rd, Harvard, MA 01451978-456-3155, piper28(at)attglobal.netAuditor:Anthony RosnerArchivistTim FrigoTrustees:Peter C. Meltzer, Michael E. Strem, DorothyPhillipsDirectors-at-LargeDavid Harris, John Neumeyer, Mary Burgess, James Phillips, Ralph Scannell, John BurkeCouncilors Alternate CouncilorsTerm Ends 12/31/2014Katherine Lee C. Jaworek-LopesMichael P. Filosa Lawrence ScottDoris Lewis John PodobinskiMorton Z. Hoffman Stuart LevyPatrick Gordon Mukund ChorghadeMary Burgess Sonja Strah-PleynetTerm Ends 12/31/2015 Catherine E. Costello Jerry JasinskiRuth Tanner Stephen LantosKen Mattes Norton P. PeetMichaeline Chen Wilton VirgoJackie O’Neil VACANT Term Ends 12/31/2016Michael Singer Sophia R. SuMary Shultz Leland L. Johnson, Jr.Robert Lichter Mary MahaneyHeidi Teng Andrew ScholteMarietta Schwartz Raj Rajur

ContentsChem Camp from the Other Side __________________________2By Jacob SandersMonthly Meeting _______________________________________52013 Nobel Prize Winner Martin Karplus of Harvard University to speak at theCambridge/Boston Courtyard MarriottMartin Karplus ________________________________________5By Jack DriscollAnnouncements ______________________________________7,8Nominations wanted for the Theodore William Richards Award for Excellence inTeaching Secondary School Chemistry and the James Flack Norris Award forOutstanding Achievement in the Teaching of ChemistryNorris Award Symposium at the Dallas Meeting ____________8,9NESACS Candidates for 2014 ____________________________9Summer Scholar Report ________________________________10Applying Green Chemistry Principles in the Electrophilic Bromination of Indole-3-Acetic AcidBy Kyle Murphy and Edward J. Brush, Bridgewater State UniversityJanuary Meeting Report ________________________________14By Xavier Herault and Jack DriscollACS Northeastern Section at Fenway Park!_________________13Red Sox Game, Tuesday, May 6, 2014March Historical Events in Chemistry _____________________15By Leopold May, Catholic University of AmericaNortheastern Student Research Conference ________________20Cover: March Speaker and 2013 Nobel Prize Winner in Chemistry ProfessorMartin Karplus shown in his office with Jack Driscoll, Public Relations Chairfor NESACS. See Page 5 for Dr. Driscoll's interview of Professor Karplus (Photocourtesy of Jack Driscoll).Editorial Deadlines: May 2014 Issue: March 15, 2014

September 2014 Issue: July 15, 2014May 2014 Issue: March 15, 2014

All Chairs of standingCommittees, the editor of THE NUCLEUS, and the Trustees of SectionFunds are members of theBoard of Directors. AnyCoun cilor of the American Chemical Soci-ety residing within the section area is an exofficio member of the Board of Directors.

4 The Nucleus March 2014

After the first night, the ChemCamp routine begins in earnest the fol-lowing morning: breakfast, four hoursof lecture, lunch, four hours of labora-tory, dinner, study and relaxation timein the evening, lights out. On top ofthis standard routine, which lasts tendays, are piled three exams, one finalexam, and two lab practical exams.

As Peer Mentor, I attended all ofthe morning lectures with the students.My main goal was to help the studentsbridge the gap between the theoreticallecture material and the level of hands-on problem solving expected in thePreparatory Problems. During eachlecture break, I would announce whichPreparatory Problems the studentswere prepared to attempt and the stu-dents would come to me with ques-tions. Near the end of the camp, I alsogave three lectures focusing on analyti-cal chemistry: advanced equilibriumtechniques, advanced titrations, and amore general how-to-solve-a-problem-when-you-have-no-idea-what’s-going-on lecture.

One thing that really distinguishes

Chem Campers from other students Ihave taught, including most Harvardundergraduates, is how demandingthey are—in the best way possible.They never left any academic stoneunturned. If a lecturer skipped steps ina derivation, students would clusteraround the blackboard during the breakto fill in the missing steps. Similarly,many students loved taking assignedproblems and making them harder:What if you dropped a key assump-tion? Could the result be generalized?I often found that, rather than teachingthese students, I ended up interactingwith them as colleagues—participatingexcitedly in the give-and-take of theirdiscussions, but letting them guide the

way. I think this is the only group ofstudents I have ever had that was moretalkative inside the classroom than out-side of it.

After lunch, the students typicallyspent the full afternoon working in thelaboratory. While I occasionallyobserved the students and assistedthem with instrumentation, as a theo-rist, I ultimately left most of the labo-ratory responsibilities to thementors—who did a fantastic jobpreparing the students for the practicalexam at the International ChemistryOlympiad. Instead, I used the after-noons to prepare for the evenings:researching the answers to particularlytough student questions and cullingthrough old International ChemistryOlympiad exams to satisfy the stu-dents’ endless thirst for more practiceproblems.

After dinner, in the evenings, thestudents could finally relax. Games ofmafia proved especially popular and,by the end of the camp, we had com-plicated the standard rules so muchthat I was at my wit’s end to imple-ment them correctly. Even during thisevening relaxation, the uniquely cre-ative talents of the students shonethrough: two of them went off todevelop a mathematical model to findthe optimal number of mafia membersneeded to make the game as fair aspossible. Many of the students, even

2013 NESACS Golf SponsorsLSNE Lyophilization Services of NE Strem Chemical Litman Gerson Sage Chemical DavosPrime OrganicsBrian O’Reilly, LLP, Patent LitigationJohnson MattheyIRIX PharmaceuticalsCambridge Major O’Conner Carnathan and Mack, LLCEdelstein and Co.Chengda - Social Hour Sponsor

continued on page 16

Chem CampContinued from page 2

Stephen Ting, Saaket Agrawal, and Jessica Xuworking together at the whiteboard during abreak in lecture.

The Nucleus March 2014 5

Monthly MeetingThe 939th Meeting of the Northeastern Section of the AmericanChemical Society

Motion: Hallmark of Life. From Marsupials to MoleculesDr. Martin Karplus, Theodore William Richards Professor of Chemistry,Emeritus, Department of Chemistry and Chemical Biology, Harvard Uni-versity and Professeur Conventionne, Université de Strasbourg, France,2013 Nobel Prize in Chemistry

Thursday, March 6, 2014Courtyard Marriott – Boston/Cambridge

777 Memorial Drive, Cambridge, MA 02139Agenda

4:30 Board Meeting in “Great Room”

5:30 Social Hour in “The Ballroom”

6:30 Dinner in “The Ballroom”

7:30 Welcome, Dr. Catherine Costello, NESACS Chair Introduction, Dr. John N. Driscoll, NESACS Public Relations ChairEvening Lecture: Dr. Martin Karplus

THE PUBLIC IS INVITED For those would like to join us for dinner, please make a reservation by noon,Thursday, February 27 using PayPal: http://acssymposium.com/paypal.html.Select the pay with credit or debit card option and follow the additional instruc-tions on the page. Cost: Members, $30; Non-members, $35; Retirees, $20;Students, $10.

If you wish, join us for the evening program only, starting at 7:30 PM.Please pre-register using PayPal http://acssymposium.com/paypal.html. Selectthe “Seminar Only” option. The fee is $1. New members or those seekingadditional information, contact the NESACS administrative secretary, AnnaSinger, at [email protected] (preferred) or (781) 272-1966, 9 AM - 6 PM.Dinner reservations not cancelled at least 24 hours in advance must be paid.Parking:Parking in the Courtyard Boston Cambridge Marriott is free of charge for thoseattending this event. u

MartinKarplusBy Jack Driscoll, NESACS Public Relations ChairThe information for this article wastaken from an interview with Prof.Karplus in January 2014, an article thathe wrote in 2006 (Annual Review ofBiophysics 35, 1-47, 2006) and theNobel Prize website.Nobel Prize BackgroundThe Nobel Prize is awarded to “theperson or persons who have made themost important chemical discovery orimprovement.” The Nobel Prize inChemistry for 2013 was awardedjointly to Martin Karplus (Universitéde Strasbourg, France, and HarvardUniversity), Michael Levitt (StanfordUniversity School of Medicine), andArieh Warshel (University of SouthernCalifornia) for their work on “thedevelopment of multiscale models forcomplex chemical systems” (http://www.nobelprize.org/).

Karplus says, “If you like to knowhow a machine works, you take it apartand put it together again. We do thatfor molecules.”

The Nobel Prize in Chemistry hasbeen awarded to 166 Laureates sinceits inception in 1901 (http://www.nobelprize.org/nobel_prizes/facts/chemistry/ ). The average age of all Chem-istry Laureates at the time of the awardis 58 years. Only four women havereceived the Nobel Prize in chemistry:Marie Curie (1911), Irène Joliot-Curie(1935), Dorothy Crowfoot Hodgkin(1964), and Ada Yonath (2009). , Tenwomen have received a Nobel Prize inPhysiology or Medicine

Martin Karplus delivered hisNobel Lecture on 8 December 2013, atAula Magna, Stockholm University,where he was introduced by ProfessorSven Lidin, Chairman of the NobelCommittee for Chemistry (http://www.nobelprize.org/nobel_prizes/chemistry/laureates/2013/karplus-lecture.html) .

Some excellent background mate-rial on his life and his research was

Copyright © Nobel Media AB 2013, Photo: Niklas Elmehed

continued on page 6

6 The Nucleus March 2014

described by Martin Karplus in a 2006article in the Annual Review of Bio-physics (http://www.annualreviews.org/doi/pdf/10.1146/annurev.biophys.33.110502.133350).

There are a number of videos onMartin Karplus that can be found onhttp://www.youtube.com in whichMartin talks about winning the NobelPrize: (http://www.youtube.com/watch?v=C5mpmPZGChA) . Martinexplains his work to young students(http://www.youtube.com/watch?v=HcN02yYerCg), and describes how hestays creative (http://www.youtube.com/watch?v=9zM3dF5GYg0 ).

A 45-minute interview of him canbe found at http://www.nobelprize.

org/podcast/. For more information,just Google Martin Karplus+ Nobelprize. A photo of the Nobel Medal is shownin Figure 1BiographyMartin Karplus was born in Austria in1930 and the family lived there untilthe German occupation of Austria in1938. The family lived in Brightonwhen they first immigrated to the U.S.but moved to Newton because of a bet-ter school system. How did he get from there to here?1. Family background

Martin’s maternal and paternalgrandfathers were both physicians. Hisfather was a mechanical engineer andhis mother worked as a nurse for herfather. His uncle invented the “Variac”or variable transformer which has beenused by most chemists. A friend intro-duced him to the Lowell lectures. Twoof Martin’s daughters are physicians.His brother Robert was an eminent the-oretical physicist and was deeplyinvolved in science education in hissecond career.

2. Early yearsMartin’s interest in biology was

stimulated by receiving a microscopeat an early age, by his father’s interestin nature, by attending the Lowell lec-tures, and by his interest in birds.

Martin had a supportive environ-ment in Newton elementary and juniorhigh schools. In high school, where hisbrother Robert had been an excellentstudent, the teachers presumed thatMartin would not be the student thathis brother had been. Martin had con-siderable problems interacting with thechemistry teacher in particular.

His brother suggested to him thathe take the Westinghouse Science Tal-ent Search exam. After he could notget a recommendation from his chem-istry teacher, he went to the principal,took the test, and became a Westing-house Scholar. 3. College

Martin attended Harvard as aWestinghouse scholar. He wasexpected to go into medicine, but dur-ing his freshman year he felt that acareer in the sciences would be moreinteresting and productive. He wasinterested in biology but chose theunique Chemistry and Physics Pro-gram at Harvard to give him a betterunderstanding of biology. I amamazed that Martin, in his freshmanyear of college, was able to select thecourses and direction of his career atsuch a young age.

Martin attended graduate school atCalifornia Institute of Technology. Hestarted as a biology major but thatchanged quickly as a result of the firstseminar he gave; his advisor said thatit was the worst seminar that he everheard. Martin was devastated, butanother Professor told him that “hesays this to everyone” and that Del-bruck probably did not understandwhat Martin had said. In any event,Martin decided to switch to chemistryand went to work under Kirkwood.Several months later, Kirkwoodaccepted an offer from Yale and invitedhis students to join him. Prof. LinusPauling had stopped taking graduatestudents but he asked Kirkwood’s stu-dents if they wanted stay at Cal Tech

Martin KarplusContinued from page 5

continued on page 17

Figure 1. Nobel Medal

THEODORE WILLIAM RICHARDS AWARDFOR

EXCELLENCE IN TEACHINGSECONDARY SCHOOL CHEMISTRY

January 2014

Do you know an excellent Chemistry Teacher to nominate for the 2014 Theodore William RichardsAward for Excellence in Teaching Secondary School Chemistry sponsored by the Northeastern Sectionof the American Chemical Society? We feel that there are many outstanding and exceptional Chemistryteachers in the Northeastern Section, so please take the time to nominate one of the deserving faculty mem-bers from your school.

The prestigious Theodore William Richards Award for Excellence in Teaching Secondary SchoolChemistry is presented annually to a teacher who demonstrates exceptional innovation and dedication ininspiring students, communication in the principles of chemistry in and out of the classroom, and leader-ship in influencing and mentoring other chemistry teachers. Sound like someone you know or work with?Then use the nomination form at http://www.nesacs.org to recognize that teacher’s talents.

Nominations by STUDENTS (current or former), COLLEAGUES, DEPARTMENT HEADS, or INDI-VIDUALS who choose to self-nominate are eligible for consideration. The deserving recipient will be hon-ored at the Education Night ceremony in May and presented with a $1,500 cash prize and Certificate ofRecognition.

Thank you for your attention in bringing recognition to the talented Chemistry Teachers of the Northeast-ern Section, and hopefully the next deserving recipient of the prestigious Theodore William RichardsAward will be from your school.

Please send nomination forms by April 11, 2014 to:Richards Award CommitteeAttn: Steve LantosBrookline High School115 Greenough StreetBrookline, MA 02445Email: [email protected]

Thank you,Richards Award Committee u

The Nucleus March 2014 7

ADMINISTRATIVE SECRETARY12 CORCORAN ROADBURLINGTON, MA 01803

Telephone: 781-272-1966E-Mail: [email protected]

NORTHEASTERN SECTIONAMERICAN CHEMICAL SOCIETY

NorrisAwardSymposiumat DallasMeetingIt may seem hard for some of us toimagine, but 2014 will see the award-ing of the 50th James Flack NorrisAward in Physical Organic Chemistry.This occasion is being marked with asymposium on Monday, Mar. 17, at theAmerican Chemical Society (ACS)spring national meeting in Dallas. Thesymposium was organized by E.Thomas Strom and Jeffrey I. Seemanof the ACS Division of the History ofChemistry with the Northeastern ACSSection and the ACS Division ofOrganic Chemistry as co-sponsors.The symposium is titled “Fifty Yearsof the James Flack Norris Award. TheFoundations of Physical OrganicChemistry.”

The opening comments will begiven by Section Chair Catherine

Costello. The introductory talk will begiven by section member ArthurGreenberg of the University of NewHampshire. His title is “James FlackNorris, A Pioneer in Chemical Educa-tion and His Early Contributions inPhysical Organic Chemistry.” This talkwill reveal some previously unknownmaterial on Norris. The symposiumwill also include seven talks by earlywinners of this award. Those speakersare Edward Arnett, Ronald Breslow,Andrew Streitwieser, Jr., John Brau-man, Paul Schleyer, Kendall Houk,and Michael Wasielewski.

The symposium will concludewith a panel discussion from additionalwinners of the award: Matthew Platz(the 2013 winner), John Baldwin, NedPorter, Hans Reich, John Roberts, andMichael Wasielewski again. The sym-posium will be held at the Omni DallasHotel.

This symposium honors one ofthis section’s most distinguished mem-bers, James Flack Norris, and also thisimportant award, which has kept Nor-ris’ memory green. We hope that thosesection members attending the springACS meeting will be present to heartalks from these great physical organicchemists. u

8 The Nucleus March 2014

Call forNominationsThe 2014 James Flack NorrisAward for OutstandingAchievement in the Teachingof ChemistryDeadline: April 15, 2014Nominations are invited for the 2014James Flack Norris Award, which con-sists of a certificate and an honorariumof $3,000 and is given annually by theNortheastern Section (NESACS). Thepresentation will take place at a cere-mony and dinner in November 2014,and will include a formal address bythe awardee. The Award was estab-lished in 1950 by NESACS to honorthe memory of James Flack Norris(1871-1940), a professor of chemistryat Simmons College and M.I.T., chairof NESACS in 1904, and ACS Presi-dent in 1925-26.

Nominees should have servedwith special distinction as teachers ofchemistry at any level: secondaryschool, college, and/or graduateschool. With the presentation of thefirst Award in 1951, awardees haveincluded many eminent teachers at alllevels whose efforts have had a wide-ranging effect on chemical education.The recipient will be selected from aninternational list of nominees whohave served with special distinction asteachers of chemistry with significantachievements.

A nomination in the form of a let-ter should focus on the candidate’scontributions to and effectiveness inteaching chemistry. The nominee’scurriculum vitae should be includedand, where appropriate, a list of hon-ors, awards, and publications related tochemical education. Seconding lettersmay also be included; these shouldshow the impact of the nominee’steaching for inspiring colleagues andstudents toward an active life in thechemical sciences, and attest to theinfluence of the nominee’s other activi-ties in chemical education, such astextbooks, journal articles, or other

professional activity at the local,national, and international level.

The nomination materials shouldconsist of the primary nomination let-ter, supporting letters, and the candi-date’s curriculum vitae. Reprints orother publications should NOT beincluded. The material should notexceed thirty (30) pages, and should besubmitted electronically in Adobe PDFformat through April 15, 2014 to Ms.Anna Singer, NESACS AdministrativeSecretary <[email protected]>.For more information about the Award,see <http://www.nesacs.org/awards_norris.html>.

Questions about the Award or thenomination process should be directedto the Chair of the Norris Award Com-mittee, Professor Doris Lewis,<[email protected]>. u

New MembersInvitation to attend a meetingYou are cordially invited to attend oneof our upcoming Section meetings as aguest of the Section at the social hourand dinner preceding the meeting.

Reservations for new membersand for additional information, contactthe secretary Anna Singer at (781)272-1966 between 9am and 6pm or e-mailat [email protected] u

Q. Exactly, how many awards andscholarships does NESACS sponsor?

A) One b) Two c) Many

www.nesacs.org/awards

Fifty Years Of The James FlackNorris Award

MONDAY, MAR. 17, 2014OMNI DALLAS HOTEL

8:55-9:00 a.m. Opening Remarks, Catherine Costello, Northeast-ern ACS Section

9:00-9:30 a.m. Arthur Greenberg, University of New Hampshire,“James Flack Norris, A Pioneer in Chemical Edu-cation and His Early Contributions in PhysicalOrganic Chemistry”

9:30-10:00 a.m. Edward M. Arnett, Duke, “Some ThermochemicalStudies in the 1960s and 70s”

10:00-10:30 a.m. Ronald Breslow, Columbia, “Aromaticity and Con-ductivity in Molecular Wires”

10:30-10:45 a.m. Break

10:45-11:15 a.m. Andrew Streitwieser, Jr., UC-Berkeley, “HydrogenIsotopes in Physical Organic Chemistry”

11:15-11:45 a.m. John I. Brauman, Stanford, “Adventures in Physi-cal Organic Chemistry”

11:45 a.m.-1:55 p.m. Lunch Break

1:55-2:00 p.m. Opening Remarks, Jeff Seeman, Moderator

2:00-2:30 p.m. Paul Schleyer, Georgia, “Norbornyl Cations StillFascinate”

2:30-3:00 p.m. Kendall N. Houk, UCLA, “Physical Organic Chem-istry with Computations: Pericyclic Reactions”

3:00-3:15 p.m. Break

3:15-3:45 p.m. Michael Wasielewski, Northwestern, “Understand-ing Electron Transfer Reactions: A Case Study inPhysical Organic Chemistry”

3:45-4:45 p.m. Panel Discussion, “Whither Physical OrganicChemistry?”Panelists: John Baldwin, Matthew Platz, NedPorter, Hans Reich, John Roberts, MichaelWasielewski u

The Nucleus March 2014 9

NESACSCandidatesfor 2014Chair

Jerry P. JasinskiWilton Virgo

SecretaryMichael Singer

TreasurerJames U. Piper

TrusteeJack DriscollRuth Tanner

AuditorAnthony L. Rosner

Councilor/Alternate CouncilorMary BurgessMukund S. ChorghadeMorton Z. HoffmanPatricia A. MabroukMichael FilosaPatrick GordonLiming ShaoChristine Jaworek-LopesDoris I. LewisChris MoretonJohn PodobinskiMary Jane ShultzSonja Strah-PlaynetAnna Waclawa SromekMark TebbeRalph T. ScannellAndrew Scholte

Director-at-Large Ralph T. ScannellJohn BurkeAndrew Scholte

Nominating Committee Mukund S. ChorghadeAnna Waclawa SromekJohn Williams

Norris Award Mary A. MahaneyMark TebbeChris MoretonRobert Goodnow

Petition Candidates: “Any group com-prising 2 per cent or more of the North-eastern Section (136 members) maynominate candidates…” See NESACSwebsite for details. u

10 The Nucleus March 2014

IntroductionThe goals of green chemistry are to reduce or eliminate theuse of hazardous reagents, prevent the synthesis of toxicproducts and byproducts, and improve the overall efficiencyof chemical reactions. Green chemistry is incredibly impor-tant today as chemical products are produced and usedaround the world, resulting in the use and generation of haz-ardous chemicals, and unintended consequences to humanhealth and the environment. Paul Anastas and John Warnerdeveloped the 12 Principles of Green Chemistry1, Figure 1,to provide the framework for a sustainable future in thedesign of more efficient technologies to produce consumerproducts that are better, safer and cheaper.

3-Bromooxindole-3-acetic acid (BOAA) is an impor-tant intermediate in our group’s work on the synthesis ofsmall-molecule mechanism-based enzyme inhibitors.BOAA is readily transformed into a variety of oxindole

derivatives designed to inhibit specific enzymes known tobe therapeutic targets, Figure 2.

The traditional method to synthesize BOAA fromindole-3-acetic acid (IAA) is illustrated in Figure 3.2 N-bro-mosuccinimide (NBS) serves as brominating agent, and tert-butanol is both solvent and reactant, providing the C-2oxindole oxygen. We have found major complications withthis synthesis, including the use and generation of hazardouschemicals, poor atom economy (30%), and low percentyield (25%). NBS is a major source of the waste byproductsincluding HBr and succinimide (see box in Figure 3). Notethat of the 24 atoms in two mole equivalents of NBS, onlyone bromine atom is incorporated in the final BOAA prod-uct, contributing to the low atom economy. Based on litera-ture precedent,3,4 we suspected that the low percent yieldwas primarily due to poor regioselectivity in the bromina-tion of IAA, resulting in the formation of isomeric bromi-nated products.

Summer Scholar ReportApplying Green Chemistry Principles in the Electrophilic Bromination of Indole-3-Acetic AcidKyle Murphy and Edward J. Brush, Department of Chemical Sciences, Bridgewater State University, Bridgewater, MA

Figure 1. The Twelve Principles of Green

Figure 2. Potential mechanism-based inhibitors based onoxindole derivatives.

Figure 3. Traditional method to synthesize BOAA from IAA.

The goal of this research project was to obtain a betterunderstanding of the overall BOAA synthetic process, andapply the Principles of Green Chemistry to improve reactionefficiency. Utilizing 1H NMR we have: identified four majorproducts from IAA bromination, determined that the reac-tion process occurs in two discrete steps, and obtained keymechanistic insight that is helping us improve on the overallefficiency of this reaction. ExperimentalAll reagents were purchased from Sigma-Aldrich or FisherScientific and used without further purification. Tert-butanolwas stored over 3Å molecular sieves. Nuclear MagneticResonance (NMR) spectra were obtained on a JEOL ECX-400 MHz instrument.

Evaluating different reaction parameters for the synthe-sis of BOAA would require substantial amounts of solventand reagents, produce liters of hazardous waste, and anentire day would be needed to run and analyze a single reac-tion. To optimize our “green chemistry” approach, wedeveloped a quick, reproducible and efficient reactionscreening method that required milliliters of solvent, mil-ligrams of reagents, and minimized waste. The screeningmethod used quantitative NMR (qNMR)5 to determine %yield and recovery. In qNMR the quantity of a particularanalyte could be determined by comparing the integratedvalue of an analyte signal of known number of H’s to theintegrated value of the vinyl protons (2H, 6.33 ppm) of themaleic acid internal NMR reference standard.6

The standard screening reaction used 200 µL of a 0.174M solution of IAA in tert-butanol (6.11 mg, 34.9 µmole)added to a 10 mL reaction vial with an additional 800 µL oftert-butanol. The solution was stirred at room temperatureand reaction initiated by the addition of two mole equiva-lents (12.4 mg, 69.8 µmole) of NBS. After stirring for anadditional 10 minutes, the reaction was worked up by evap-oration of tert-butanol solvent on a high vac, and then sus-pending the residue in diethyl ether. The succinimidebyproduct was removed by pipette filtration into a 10 mLround bottom flask and solvent again evaporated underreduced pressure. Acetone-d6 containing 0.05% TMS (1.0mL) was added to dissolve the residue, then 2.00 mg(0.0172 mol) of maleic acid dissolved in 25 µL of dimethyl-sulfoxide-d6 was added as the internal qNMR referencestandard. This screening method allowed us to run and ana-lyze up to five reactions per day. This general procedureallowed us to test the effect of various reaction parameterson the product distribution, including the IAA:NBS stoi-chiometry, and addition of potential catalysts.Results and DiscussionThe traditional reaction mixture with two equivalents ofNBS was worked up to remove residual solvent and succin-imide byproduct, and the residue analyzed by 1H NMR, Fig-ure 4. By focusing exclusively on signals in the aromatic

region, we were able to identify four major products fromIAA bromination, Figure 5.

We propose that the bromination of IAA with twoequivalents of NBS occurs in two reaction steps as shown inFigure 6. In Reaction #1 the initial equivalent of elec-trophilic bromine adds rapidly (within seconds) to the C-2,3double bond (possibly with assistance from N-1), followedby addition of tert-butanol to C-2. Subsequent eliminationsteps (mechanism not shown) produce oxindole-3-aceticacid (OAA). We also observe 5-bromo-OAA most likelyfrom the addition of a second equivalent of bromine to C-5of OAA (consistent with literature precedent7). Reaction #2is slow addition of the second equivalent of NBS to C-3,producing BOAA and 5-bromo-BOAA. Our proposal isconsistent with the observation of C-3 and C-5 brominatedproducts from indoles.3,4,7 The C-3 position of indoles isknown to undergo bromination very rapidly, while C-5bromination was based on the known activating effects ofthe N-1 nitrogen (C-7 brominated product was notobserved). The authors from these original studies employedindirect methods for product analysis based on chemicaltransformation to known compounds, followed by meltingpoint determination. Our work is the first to conclusivelyidentify the IAA bromination products using 1H NMRanalysis.

The Nucleus March 2014 11

Figure 4. 1H NMR (400 MHz) of IAA reaction with twoequivalents of NBS.

Figure 5. Oxindole byproducts of complete IAA-NBS reac-tion: (a) 3,5-dibromooxindole-3-acetic acid (5-Bromo-BOAA), (b) 3-bromooxindole-3-acetic acid (BOAA), (c)5-bromooxindole-3-acetic acid(5-Bromo-OAA), (d) oxin-dole-3-acetic acid (OAA).

continued on page 12

Summer ScholarContinued from page 10

To test this idea we ran the traditional BOAA synthesis fromIAA by adding NBS in two separate steps. The results ofthese reactions (data not shown) clearly show that additionof one mole equivalent of NBS produces OAA and 5-bromo-OAA. Subsequent addition of a second NBS equiva-lent gives the typical product distribution shown in Figure 5.

As our preliminary data suggested that addition of thefirst equivalent of electrophilic bromine to IAA was the crit-ical step, in that multiple oxindole byproducts are producedand that this poor regioselectivity was ultimately responsiblefor the poor efficiency of this reaction. As we could nowsuccessfully run the BOAA synthesis as two separate reac-tions (Figure 6), this allowed us to focus exclusively onReaction #1, and conduct preliminary experiments toimprove the poor regioselectivity.

It has been reported that the selectivity of NBS-medi-ated brominations can be controlled with amides andamidines that act as Lewis base catalysts by either facilitat-ing the regioselective transfer of bromine from NBS to theacceptor, or stabilizing the bromonium ion intermediate.8-11

Furthermore, in the traditional synthesis we suspected thatHBr generated during the course of Reaction #1 catalyzesC-3 halogenation of OAA through an enol intermediate. Wesubsequently surveyed a variety of Lewis base, and acid cat-alysts for improving the overall efficiency of BOAA synthe-sis. Representative data are presented in Table I.

When dimethylformamide (DMF) was added to Reac-tion #1 there was modest improvement in the regioselectiv-ity by promoting BOAA production as compared to theoxindole byproducts. Similar results were obtained whenacetic acid was added to Reaction #2, consistent with acidcatalyzed halogenation. Furthermore, addition of triethy-lamine inhibited production of BOAA as well as other oxin-dole byproducts, possibly by neutralizing any HBr producedin Reaction #1.Conclusions and Future WorkWe have applied Green Chemistry principles and NMRanalysis to better understand the synthetic reactions in thepreparation of BOAA from IAA. We have identified fouroxindole products from this reaction, and determined thatIAA bromination occurs in two discrete steps. These prelim-

inary results have provided key mechanistic insight that willhelp us improve the low yield and overall efficiency of thisreaction. We are currently evaluating additional Lewis basecatalysts to improve the regioselectivity in Reaction #1, andthe effect of acid catalysts for Reaction #2. We are also veryinterested in developing an efficient gram-scale synthesis ofoxindole-3-acetic acid (OAA) in Reaction #1, as this com-pound has recently been identified in the regulation of auxinhomeostasis and response mechanisms in plants.12

AcknowledgementsThis research was supported by a 2013 Norris-RichardsSummer Scholarship awarded by NESACS, and a Bridge-water State University Center for Sustainability summer2012 grant. The author would like to thank his researchmentor Dr. Edward Brush, and Dr. Steven Waratuke for hisAdvanced NMR class. The JEOL ECX-400 MHz NMR wasobtained through NSF-MRI grant 0421081.References1Anastas, P. T.; Warner, J. C. Green chemistry: theory andpractice; Oxford University Press: Oxford [England]; NewYork, 1998.2Hinman, R.L and Bauman, C.P. (1964), “Reactions of N-Bromosuccinimide and Indoles. A simple synthesis of 3-bromooxindoles,” J. Org. Chem. 29, 1206-1215.3Lawson, W.B., Patchornik, A., and Witkop, B. (1960),“Substitution, oxidation and group participation in thebromination of indoles,” J. Amer. Chem. Soc., 82: 5918-23.4Condie, G.C., Channon, M.F., Ivory, A.J., Kumar, N. andBlack, D.St.C. (2005), “Regioselective reactivity of some5,7-dimethoxyindoles,” Tetrahedron, 61(21): 4989-5004.5Peterson, J. (1992), “1H NMR Analysis of Mixtures UsingInternal Standards,” J. Chem. Educ., 69 (10): 843-5.6JEOL Resonance Application Note NM090009E (2011),“What is qNMR (quantitative NMR)?” www.jeol.co.jp(accessed October 2013).7Sumpter, W.C., Miller, M., and Hendrick, L.N. (1945), “Astudy of certain brominated derivatives of oxindole”, J.Amer. Chem. Soc., 67(10): 1656-8.

12 The Nucleus March 2014

continued on page 13

Summer ScholarContinued from page 11

Figure 6. Proposed reaction scheme for IAA bromination. Table I. %Composition of oxindole products as a functionof reaction conditions

The Nucleus March 2014 13

8Denmark, S.E. and Burk, M.T. (2010),“Lewis base catalysis of bromo- andiodolactonization, and cycloetherifica-tion,” Proc. Natl. Acad. Sci. USA,107(48), 20655-20660.9Pathak, T. P. and Miller, S. J. (2012),“Site-selective bromination of van-comycin,” J. Amer. Chem. Soc., 134,6120-6123.10Ahmad, S. M., Braddock, D. C.,Cansell, G., Hermitage, S. A., Red-mond, J. M., and White, A. J. P.(2007), “Amidines as potent nucle-ophilic organocatalysts for the transferof electrophilic bromine from N-bro-mosuccinimide to alkenes,” Tetrahe-dron Letters, 48, 5948-5952. 11Ahmad, S. M., Braddock, D. C.,Cansell, G. and Hermitage, S. A.(2007), “Dimethylformamide,dimethylacetamide and tetramethyl-guanidine as nucleophilic organocata-lysts for the transfer of electrophilicbromine from N-bromosuccinimide toalkenes,” Tetrahedron Letters, 48, 915-918.12Pencik, A., Simonovik, B., Petersson,S.V., Henykova, E., Simon, S., Green-ham, K., Zhang, Y., Kowalczyk, M.,Estelle, M., Zazimalova, E., Novak,O., Sandberg, G., and Ljung, K.(2013), “Regulation of auxin home-ostasis and gradients in Arabidopsisroots through the formation of theindole-3-acetic acid catabolite 2-oxin-dole-3-acetic acid,” Plant Cell, Octo-ber 25 Epub ahead of print,http://www.plantcell.org/content/early/2013/10/23/tpc.113.114421.full.pdf(checked November 2013). u

Summer ScholarContinued from page 12

JoinNESACS

on facebookwww.facebook.com/nesacs

ACS Northeastern Sectionat Fenway Park!Red Sox Game Tuesday, May 6

Northeastern Section members are encouraged to bring their families, friends,and colleagues to this NESACS traditional outing. We are hoping again this yearfor pleasant weather, good company, and a winning team.

On Tuesday, May 6th we have right field box seats for the Red Sox - Cincin-nati Reds game. Our tickets reflect the lowest possible cost under the new RedSox ticket pricing policy; $45 includes handling charges and a small donation tothe Northeastern Section. Reserve your seats by mailing your check (payable toNESACS) to Anna Singer, 12 Corcoran Road, Burlington, MA 01803. Questionsmay be sent to [email protected]. u

Fenway park photo from Boston.redsox.mlb.com

14 The Nucleus March 2014

JanuaryMeetingReportBy Xavier Herault (with additionalcontent and photos provided byJack Driscoll)The 937th Meeting of the NortheasternSection of the American Society washeld at the Holiday Inn in Brookline onThursday, January 16, 2014. Thespeakers were Dr. Heidi Erlacher, apartner at the law firm Mintz Levin,Cohn, Ferris, Glovsky and Popeo, P.C.Christopher Montean, a tax accountantat Ernst & Young and Dr. EddineSaiah, the Head of Chemistry at AtlasVenture, a venture capital firm. Dr.Monica Palme, a Sr. Director of DrugDevelopment at Pfizer who was slatedto speak, unfortunately, could notmake it.

The subject of the symposium was“Alternate Careers for Chemists, orWhat Do I Want to Be When I GrowUp?” NESACS Chair, Cathy Costelloopened the meeting and ProgramChair, Katherine Lee was the modera-tor.

The three speakers first describedwhen and how they knew it was timefor them to move their careers into anew direction after practicing chem-istry. Each has taken a different route.For Dr. Heidi Erlacher, it was duringher doctoral work at the MassachusettsInstitute of Technology. For Christo-pher Montean, it was while a few yearsinto his chemistry career at Corning.For Dr. Eddine Saiah, it was after atwenty-year career in medicinal chem-istry that saw him reach the position ofDirector of Chemistry at Pfizer inCambridge. However, the commontheme for all was the realization that alife in the lab or in meetings was notfor them anymore and that their otherinterests (law, finance or starting newbiotech companies) were stronger.

Each speaker offered words ofadvice to other chemists consideringmaking a change. You never knowwho you can meet in your everyday

life who will open your mind to newopportunities (Dr. Heidi Erlacher).Sometimes it can be a big change butyou need to learn to be comfortablebeing in an uncomfortable time ofchange (Christopher Montean). At theend, you don’t choose a job, the jobchooses you (Dr. Eddine Saiah).

A transition to a career in the lawcould be either going to law schoolright after the doctorate, or starting in alaw firm as a technical advisor andgoing to law school part-time in theevening. A change to a career infinance would require going back toschool to pursue a Master’s in account-ing and maybe even a concurrentMBA. A jump to business and being aventure capitalist would require cash-ing in during a very successful scien-tific career.

After the panelists described theirsituations, the floor was opened to theaudience. The questions continued fornearly an hour before the meeting wasclosed.

NESACS PR Chair, Jack Driscolltalked for a few minutes about theACS Entrepreneurial Forum whichwill be held on April 9, 2014. A videoabout this forum can be found onYouTube: (http://youtu.be/jmSiy-cZpCnY)

NESACS thanks the speakers forsharing their unique insights into tran-sitioning into alternate careers.

Sixty-five registered for the meet-ing. Please remember you must regis-ter one week before a meeting whether

or not you intend to have dinner. After dinner an additional 50 stu-

dents arrived to attend the symposiumand take advantage of the NESACSpolicy that the evening program is freeand open to the public. This meetingwas an excellent start for our new pro-gram chair, 2014 Chair-elect, Kather-ine Lee. u

NESACS Chair-Elect and Program Chair,Katherine Lee Moderating the Panel on alterna-tive careers for chemists. Pictured (L-R) areKatherine Lee, Heidi Erlacher, ChristopherMontean and Eddine Saiah.

NESACS Chair Cathy Costello opening the937th NESACS Monthly Meeting

What’s Yours?

DMPK Scientist, LC/MS Product Specialist,

Mass Spec Operator, Staff Investigator, Process Chemist,

QA Manager, Synthetic Chemist, Lab Instructor . . .

Many local employers post positions on the NESACS job board.

Find yours atwww.nesacs.org/jobs

MarchHistoricalEvents inChemistryBy Leopold May, Catholic Univer-sity of AmericaMarch 1

b. 1910 Archer J. P. Martin, NobelPrize (1952) with Richard L. M.Synge for their invention of partitionchromatography.

March 3b. 1918 Arthur Kornberg, researcheron the synthetic pathways by whichnucleic acids are produced; NobelPrize in Medicine (1959) withSevero Ochoa for their discovery ofthe mechanisms in the biologicalsynthesis of ribonucleic acid anddeoxyribonucleic acid.

March 8b. 1879 Otto Hahn, discovered pro-tactinium (Pa, 91) with L. Meitner;researcher on nuclear fission with F.Strassman (1938); Nobel Prize(1944) the discovery of fission ofheavy nuclei.b. 1886 Edward C. Kendall isolatedthyroxine, 1915; Nobel Prize inMedicine (1950) with Philip Hench& Tadeus Reichstein for their dis-coveries relating to the hormones ofthe adrenal cortex, their structure andbiological effects.

March 9b. 1923 Walter Kohn, developeddensity-functional theory, whichmakes it possible to study very largemolecules; Nobel Prize (1998) withJohn A. Pople for his development ofthe density-functional theory

March 14b. 1854 Paul Ehrlich, researcher inimmunity & chemotherapy; discov-ered Salvarsan (No. 606) & neosal-varsan; improved laboratory stainingmethods; Nobel Prize in Medicine(1908) with Ilya Ilyich Mechnikov inrecognition of their work on immu-

nity.b. 1879 Albert Einstein, researcheron photochemical effect & theory ofrelativity; Nobel Prize Physics(1921) for his services to TheoreticalPhysics, and especially for his dis-covery of the law of the photoelec-tric effect.

March 19b. 1883 Walter N. Haworth, synthe-sized ascorbic acid (Vitamin C),1933; researcher on sugars & dextranas blood plasma substitute; NobelPrize (1937) for vitamin synthesis,with Paul Karrer. b. 1900 Frederic J. Joliot (Joliot-Curie), Nobel Prize, (1935) withwife Irene Joliot-Curie, for produc-tion of artificial radioisotopes, in1934; proved experimentally thatneutron emission occurs in nuclearfission with H. Halban & L. W.Kowarski. b. 1943 Mario Molino, researcher inair pollution, particularly formation& destruction of ozone; Nobel Prize(1995) with Paul Crutzen & F. Sher-wood Rowland for their work inatmospheric chemistry, particularlyconcerning the formation anddecomposition of ozone.

March 21b. 1932 Walter Gilbert, researcher onthe determin-ation of deoxyribonu-cleic acid (DNA) base sequence;Nobel Prize (1980) with Paul Berg &Frederick Sanger for their contribu-tions concerning the determinationof base sequences in nucleic acids.

March 22b. 1868 Robert A. Millikan measuredthe charge/mass ratio of the electron;Nobel Prize in Physics (1923) “forhis work on the elementary charge ofelectricity and on the photoelectriceffect”.

March 23b. 1881 Hermann Staudinger, re -searcher on the chemistry of macro-molecular substances; Nobel Prize(1953) for his discoveries in the fieldof macromolecular chemistry

March 24b. 1903 Adolf F. J. Butenandt,researcher on sex hormones; offered

Nobel Prize (1939), for his work onsex hormones; declined on account ofNazi decree against foreign awards.b. 1884 Peter Joseph William Debye,researcher in dipole moments andpowder method of x-ray diffraction;Nobel Prize (1936) for his contribu-tions to our knowl-edge of molecularstructure through his investigationson dipole moments and on the dif-fraction of X-rays and electrons ingases.b. 1917 John Kendrew, research onstructure of hemoproteins with x-rays; Nobel Prize (1962) with MaxFerdinand Perutz for their studies ofthe structures of globular proteins

March 26b. 1911 Bernard Katz, Nobel Prize inMedicine or Physiology (1970) withJ. Axelrod and U. Von Euler for dis-coveries concerning humoral trans-mittors in the nerve terminals and themechanism for their storage, releaseand inactivation.b. 1916 Christian Anfinsen, receivedthe Nobel prize (1972) with Stand-ford Moore and William Moore, forstudies on the relationship of struc-tural properties of proteins and bio-logical functions, particularlyribonuclease.

March 27b. 1845 Wilhelm K. Rontgen discov-ered X-rays, 1895; Nobel Prize inPhysics (1901) in recognition of theextra-ordinary services he has ren-dered by the discovery of the remark-able rays subse-quently named afterhim; researcher in specific heats &heat conduction in crystals.b. 1847 Otto Wallach, researcher onessential oils & terpenes; NobelPrize (1910) in recognition of hisservices to organic chemistry and thechemical industry by his pioneerwork in the field of alicyclic com-pounds. 1847-1931

March 31b. 1890 W. Lawrence Bragg,researcher in X-ray & crystal struc-ture; Nobel Prize in Physics (1915)with father, William H. Bragg fortheir services in the analyses of crys-tal structures by means of X-ray. u

The Nucleus March 2014 15

16 The Nucleus March 2014

while relaxing, were still chewingaway on a tricky problem—and some-times this would erupt without warninginto a full discussion. I think theseunplanned moments—with the linecompletely blurred between chemistryand hanging out—were the highlightof the camp. Where else but ChemCamp, after all, could this line be soblurred? For me, at least, this perma-nently blurry line between chemistryand camaraderie is the defining aspectof Chem Camp.

Lights out marked the end of ajam-packed day for the students. Butfor the mentors and me, lights out wasa new beginning. With lectures to pre-pare, laboratory write-ups to finalize,practice problems to find, and examsto write and grade, all of us had morethan enough work to keep us burningthe midnight oil long past midnight.With exams ranging from thirty to fiftypages, and involving some of the hard-est and most creative chemistry prob-lems, perhaps the only thing harderthan taking the exams is writing them.Even with generous help from the AirForce Academy faculty in their areasof expertise, I think it would be fair tosay that the mentors all felt a sense ofpride (and exhaustion!) after eachexam—only to start all over again thenext day. The first thing I did when Ireturned home after Chem Camp wasto go to sleep—uninterrupted—for along time.

The last few days of the camprushed by in a sleepless haze: an outingto the beautiful Garden of the Godspark, an elaborate closing banquet atwhich the top six students areannounced, emotional good-byes(though many of the students will bereunited in a few short months at uni-versity), a few more days spent train-ing and testing the top six students, andultimately the selection of the finalfour students on the traveling team.

But the work of the students andmentors did not end with the camp.After returning home and sleeping offall of the end-of-camp excitement, thefour students worked together for a

month before the international compe-tition to make sure they were all wellprepared. As Peer Mentor, I helped thestudents by preparing a repository ofpractice problems. Just like during thecamp, I was amazed by how endlesswas their desire for more problems.We also created a Facebook groupwhere the students could shareresources and advice. What impressedme most was how dedicated our fourstudents were at stamping out theirweaknesses—not just individually butcollectively. With some studentsexperts on synthetic chemistry, andothers experts on mathematical chem-istry, I was blown away by the vigorwith which each side helped the otherachieve mastery. I merely helped toanswer questions and make sure theirefforts were well-directed.

Given this wonderful synergywhich developed among our students, Iam pleased—but not surprised—toreport that our team put in an outstand-ing performance in Moscow at theinternational competition, with DavidLiang and Runpeng Liu receiving goldmedals, and Stephen Ting and SaaketAgrawal receiving silver medals.

As for me, I am already countingdown the days until Chem Camp 2014!u

Chem CampContinued from page 4

Chemistry and camaraderie all blurred into one.

Your one-stop source to career-relatedlinks in the Chemical Sciences

WWW.NESACS.ORG/CAREERS

The Nucleus March 2014 17

and work with him. Martin was theonly one who chose that path. It wascertainly a wise choice for Martin’sdevelopment as a theoretical chemist.

Martin was only 23 when hereceived his PhD and was headed for atwo-year postdoc sponsored by theNational Science Foundation (NSF) atOxford. He was there to find “areaswhere theory could make a contribu-tion of general utility to chemistry.” Hedid not want to do research that wasjust of interest to theoretical chemists.By listening to lectures, talking to sci-entists, he realized that nuclear mag-netic resonance (NMR) was a vitalnew area that was in its infancy, andthat it was a field where theory couldmake a significant contribution. 4. Academic Career

He wanted to work at a Universitythat had an active experimental pro-gram in NMR. The University of Illi-nois was the obvious choice. He wasoffered an instructorship in 1955 andspent the next 5 years there. Hisresearch focused on theoretical meth-ods for relating nuclear and electronspin magnetic resonance parameters tothe electronic structure of molecules.

In 1960, he moved to Columbiawhere his focus changed to reactionkinetics. He worked in the Watson Sci-entific Lab at Columbia. He also hadan adjunct associate professorship inthe Chemistry Department at Colum-bia. A fast computer is one of the needsof a theoretical chemist and the Watsonlab had an IBM 650 computer, whichMartin put to good use.

He continued to work on NMRand ESR, and with that computer, stud-ied the reaction of H +H2 = H2 + H,which involves exchange of hydrogenatom with H2, by calculating classicaltrajectories. His paper on H + H2 wascited by George Schatz as one of thekey papers in theoretical chemistry ofthe 20th Century.

In 1966, Karplus moved to Har-vard as a Professor and in 1979, hebecame the Theodore Richards Profes-sor of Chemistry. Theodore Richardswas the first American to receive the

Nobel Prize in Chemistry in 1914. After a short time at Harvard,

Martin decided to return to his long-standing interest in biology. AriehWarshel (co-Nobel Laureate) joinedhis group at Harvard for a short time,and they worked on the retinal chro-mophore. Subsequently, he appliedmolecular dynamics methods to hemo-globin and protein folding.

Over a number of years, the soft-ware designated Chemistry at HAR-vardMacromolecularMechanics(CHARMM) was developed. In 1977it was first applied to a biomolecule(Figure 1) in {J.A. McCammon, B.R.Gelin, and M. Karplus, ”Dynamics ofFolded Proteins”, Nature 267, 585-590(1977)}. “This study has served toopen a new field that is now the focusof the research of an ever growingnumber of scientists.”

The molecular dynamics simula-tion method, which continues to bedeveloped in the CHARMM programby the Karplus group and many of hisformer students, as well as the largenumber of researchers effectivelyusing it for biomolecules provided thebasis for the 2013 Nobel prize. It isamazing that it took so long to awardthe Nobel prize for such an outstandingachievement.

Martin received grants from anumber of government agencies,

including NSF, NIH, AEC, and DOE,to fund his research. He only receiveda small amount of funding from onedrug company, because he did rela-tively little applied research.

Martin describes himself as a The-oretical Chemist. He goes to workevery day with his wife Marci, his lab-oratory manager, and still enjoys work-ing with his students at age 83. Thephoto shows Martin enjoying tea withhis students. I enjoyed the interviewwith Prof. Karplus. I thought he wasvery insightful, friendly, and generouswith his time.

It is interesting to note that noneof the 2013 Nobel Laureates in chem-istry were born in the U.S. MartinKarplus was born in Austria, AriehWarshiel was born in Israel, andMichael Levitt was born in SouthAfrica. u

Martin KarplusContinued from page 6

Figure 2. 1st Simulation of a Biomolecule using CHARMM (from Nobel Lecture)

Figure 3. Professor Karplus enjoying tea withhis students

18 The Nucleus March 2014

B U S I N E S S D I R E C T O R Y

SERVICESSERVICESSERVICES

The Nucleus March 2014 19

CAREER SERVICESCAREER SERVICES

B U S I N E S S D I R E C T O R Y

SERVICES

Index of AdvertisersChemir .............................18Drew University...............19Eastern Scientific Co. ......13Mass-Vac, Inc.....................6Micron, Inc. .....................18NuMega Resonance Labs18Organix, Inc. ....................18PCI Synthesis.....................4Rilas Technologies, Inc. ..19Robertson Microlit Labs..18Tyger Scientific, Inc. .......18Waters Corporation..........19

Check the NESACS home pagefor late Calendar additions:http://www.NESACS.orgNote also the Chemistry Department webpages for travel directions and updates.These include:http://www.bc.edu/schools/cas/chemistry/semina

rs.htmlhttp://www.bu.edu/chemistry/seminars/http://www.brandeis.edu/departments/chemistry/

events/index.htmlhttp://www.chem.harvard.edu/courses/seminars.

phphttp://chemcalendar.mit.edu/index.phphttp://chem.tufts.edu/seminars.htmlhttp://engineering.tufts.edu/chbe/newsEvents/se

minarSeries/index.asphttp://www.chem.umb.eduhttp://www.umassd.edu/cas/chemistry/http://www.uml.edu/Sciences/chemistry/Seminar

s-and-Colloquia.aspxhttp://www.unh.edu/chemistry/events

Mar 3Prof. Bill Tolman (University of Minnesota)      “Copper Oxygen Intermediates Relevant toMetalloenzymes and Other Oxidation Catalysts”Brandeis University, Gerstenzang 121 4:00 pm

Mar 4Prof. William B. Tolman (University ofMinnesota)“Copper Oxygen Intermediates Relevant toMetalloenzymes and Other Oxidation Catalysts”Boston College, Merkert 130 4:00 pmProf. Peter Seeberger, (Max Planck Institute)Tufts University, Pearson P-106 4:30 pm

Mar 5Prof. William Tolman (University of Minnesota)Boston University, Metcalf Science CenterBuilding, Rm 113 4:00 pm

Mar 6Prof. Karl Gademann (University of Basel) andDr. Chris Senanayake, Boehringer_IngelheimMIT, 6-120 4:00 pm

Mar 10Prof. Ming Hammond (University of California,Berkeley)“Privileged RNA scaffolds for the in vivosensing functions”Brandeis University, Gerstenzang 121 4:00 pm

Mar 11Prof. Ming Hammond (University of California,Berkeley)Boston College, Merkert 130 4:00 pmProf. Geert-Jan Boons (University of Georgia)Tufts University, Pearson P-1064:30 pm

Mar 12Prof. William D. Jones (University of Rochester)“Why Do Weaker Metal-Carbon Bonds Lead toMore Stable Complexes? What's Going On?”Boston College, Merkert 1304:00 PM

Mar 13Prof. Martin Burke (University of Illinois)MIT, 6-120 4:00 pm

Mar 18 Prof. Amy E. Keirstead (Univ. of New England)Univ. of Ne w Hampshire, Room N10411:10 am

Mar 20Prof. Jeff Johnson (U. of North Carolina) & Dr.David Kronenthal, Bristol-Myers SquibbMIT, 6-120 4:00 pm

Mar 21Prof. Connie Lu (University of Minnesota)“Harnessing Metal-Metal Bonds: Bonding,Electronic Properties and Small-MoleculeReactivity”Brandeis University, Gerstenzang 121 4:00 pm

Mar 24 Prof. Wenbin Lin (University of Chicago)Brandeis University, Gerstenzang 121 4:00 pm

Mar 25Prof. Michael Krische (University of Texas)Boston College, Merkert 130 4:00 pm

Mar 25Prof. Samir Z. Zard (École Polytechnique,France)MIT, 6-120 4:00 pmDr. Grace Wong (Actokine Therapeutics)“Career Decisions: Academia vs Industry, andGetting a Foot in the Door”Univ. of New Hampshire, Room N10411:10 am

Mar 27Prof. Viresh Rawal (University of Chicago)MIT, 6-120 4:00 PMProfesseur Samir Z. Zard, (École Polytechnique,France)Brandeis University, Gerstenzang 121 4:00 PM

Mar 31 Prof. Istvan Z. Kiss (Saint Louis University)Brandeis University, Gerstenzang 121 4:00 PM

Notices for The NucleusCalendar of Seminars should be sent to:Xavier Herault, email: xherault(at)netzero.net u

NO

NPR

OFIT O

RG

.U

.S. POSTA

GE PA

IDN

ORTH

EASTER

N

SECTIO

NA

MER

ICA

N C

HEM

ICA

LSO

CIETY

Calendar

19 Mill R

oadH

arvard, MA

01451

Northeastern Student ChemistryResearch Conference & Career Symposium

April 12-13, 2014Boston University

Career panels, workshops,research presentations, awards & more

Abstract deadline: March 10, 2014Registration & info: nsycc.org

Abstracts: [email protected] by:Northeastern Section Younger Chemist Committee (NSYCC)Boston University Younger Chemist Committee (BUYCC