Nomenclature

O

F

OH

N

OH

O

F

H

ClH.

(1-RS, 1’-RS)-1, 1’-[(2-RS, 2’SR)-bis(6-flurochroman-2-yl)-2, 2’-iminodiethanolHydrochloride

Nebivolol Hydrochloride

NomenclatureDr. V. A. Chatpalliwar

Prof., Pharm. Chem.Head, Dept. Pharm. Chem.S. N. J. B. Coll. Pharm.Neminagar, ChandwadDist.: Nashik

MGV’sCollege of Pharmacy

Malegoan, Nashik

Organic Compounds: Classified as Functional Groups

11/27/2011 3Dr. V. A. Chatpalliwar

A group of atoms of same/different elements, which majorly determines the properties of a compound of which it is a part.

Acetic acid

Hydrocarbons

Alcohols

Alkyl halides

Aldehydes

Ketones

Carboxlic acids

Amines

Amides Sulphonamides

Sulphonic acids

Phosphonic acidsAnhydrides

Esters Sulphates

Nitro compounds

CH3 COH

O

Why?• Discriminate each organic compound, either

known earlier or came to knowledge/existence just now, in a unique way such that organic chemist all over the world interpret exactly the compound represented by its nameso that

• The name represents elementary composition, qualitatively as well as quantitatively, and

• The name represents one (JUST ONE) compound.

11/27/2011 Dr. V. A. Chatpalliwar 4

Organizations that decide/amend rules of nomenclature

• IUPAC

• CAS– Follows IUPAC– Departs in one way intentionally; it

assigns a number Chemical Abstract Registry Number (CAS)


Nitrodipin


Structure and name and CAS of a compound

NH

O

O CH3CH3

O

CH3 CH3

N+

O-

O

1, 4-Dihydro-2, 6-dimethyl-4-(3-nitrophenyl)-3, 5-pyridinedicarboxylic acid ethyl methyl ester

39562-70-4

Expectations from a NAME

• The specific name coined for an organic compound should describe satisfactorily

• Composition and configuration of the carbon skeleton• Interruptions of carbon skeleton by

heteroatoms• State of hydrogenation of the skeleton• Presence and locations of substituent/s in in

place of hydrogen• Features of stereoisomerism


Considerations: Ambiguity, Preference, and Trivial names

Trivial names


Ambiguity

Preference:

Salicylic acid

Stereoisomerism remains un-indexed

CH3O

OH

Acetic acid

Ethanoic acid

OH

O

OH2-Hydroxybenzoic acid

CH3

NH2

OH 1-Hydroxy-2-aminopropane

2-Amino-1-Hydroxypropane

Commonly Used TermsPrefixes & Suffixes


Depending on presence, or absence, of functionality in compounds, these are named specifically in trivial names and have been used as it is, or in-part, as these make an indication towards their presence/absence in the compound.

Morphine

NHH

OH OH

NH

OH OH

CH3

Desmethylmorphine

Prefixes


Aldehydeald- Aldoxime Aldose

Close relationshipallo- Allosteric enzyme

anhydro- state without water

Ar- Aromatic

bis- 1-[bis-(4-Chlorophenyl)]-3-nitrobutane

1, 1-Dichloroheptanedi-


cyclo-

d-

D-

des-

dl

Δ presence & position of an unsaturated site in a straight chain

Prefixes

Cyclic substituent present in compounds

Indicates optical activity: dextrorotatary

Indicates a series within a family of stereoisomers

Indicates the removal of a group otherwise present in other famous molecule

Indicates presence of both optical isomers in exactly sameproportion


epi- epimer

gem- Two identical groups attached to same carbon

hetero-

hydro- presence of hydrogen atom at a position

Indicates an isomeriso-

laevo-

L-

Prefixes

Two identical groups attached to same carbon

Indicates an optical isomer

Indicates a series within a family of stereoisomers


m-

n-

N-

nor-

Ephedrine Norephidrine

Prefixes

meso- Indicates a series within a family of stereoisomers

dextro-

E-

Indicates optical activity: dextrorotatory

Indicates presence of unsaturation, geometric isomerism; Entagen arrangement

normal parent molecule

Indicates presence of group as a substituent on nitrogen

position on aromatic (phenyl) ring with respect to a substituent

Indicates absence or a group, which otherwise present in arelated molecule

Dr. V. A. Chatpalliwar 1411/27/2011

OH

H

NH

CH3

CH3

Ephedrine

OH

H

NH2

CH3

Norephidrine

OH

H

CH3

NHCH3

PseudoephidrineΨ


sym-

syn -

symmetrical positions 1, 3, 5-trihydroxybenzene

same as cis-; opposite of anti-

t- tert-

Prefixes

o -

p -

R- and S- Rectus and Sinistere



Position joined to three carbon atoms on a carbon skeleton


trans-cis-

tris-

Z-

(±)- Racemic: a sample consisting of equal proportion of bothEnantiomeric compounds

Indicates presence of unsaturation, geometric isomerism; Zuzamen arrangement

Indicates presence of three identical functional groups on a carbon atom

Indicates presence of identical functional groups present across a site of unsaturation on one/either side; in a geometric isomer

Prefixes

Suffixes


-al

-ane

-ase

-ate

-ene

-ine

aldehyde

Saturated aliphatic hydrocarbon

Name of enzyme describing its activity

Peptidase enzyme

Name of salt or ester sodium oxalate ethyl acetate

Name of an unsaturated compound Propene

Name of an amine Aniline

Butanal

Propane


Suffixes

-oic acid carboxylic acid BenzoicacidAcetic acid

ethanoic acid

-ol alcohol / phenol

-one ketone

-ose carbohydrate

-oside Glycoside Glycoside

-yl A univalent group, radical of a saturated

methyl, ethyl

-enyl A univalent group, radical of an alkene

phenyl, ethenyl


Groups

acetamido- CH3CONH- 4-acetamidophenol

acetate CH3COO- Phenyl acetate

acetoxy

acetyl

acyl

CH3CO- acetyl coenzyme A

alkyl R-

aryl Ar-

hydrazo

hydrazino-NHNH-

-NHNH2


Groups

isocyano -NC 4-acetamidophenol

mesityl 2, 4, 6- (CH3)3C6H2- Phenyl acetate

nitrate

nitro

nitroso -NO

Nitrobenzene

oxo C=O

oxy -O-

Peroxy -O-O-

Phenyl- -C6H5

Hydrogen peroxide

Phenyl acetate

-NO2

-ONO2


Groups

Salicyl o-(OH)C6H4CO- salicyl benzoate

sulphonyl -SO2- Tolylsulphonyl chloride

sulphide

Sulphonamido

Thiol -SH

Thionyl S=O

tosyl CH3C6H4SO2-

vinyl CH2 = CH-

sulphonic acid -SO2OH Benzenesulphonic acid

-S- Diethyl sulphide

-SO2NH2 sulphanilamide


Trials

Heterocyclic Compounds

Trivial names prevail and sufficiently describe heterocyclic compounds if they are not substituted.


N

Pyridine

O

Pyran

N

NH

Benzimidazole

Systematically Naming the Heterocyclic Compounds

Expectations Number of cycles: mono, poly (arrangement of cycles), fused Members in a cycle Hetero- atoms present: single or poly State of hydrogenation Numbering: to indicate the position carrying functional

group/s


N

NH

1H-Benzimidazole

Ring size N present N absentunsaturated ring saturated ring unsaturated ring saturated

ring3 -irine -iridine -iren -iran4 -ete -etidine -et -etan5 -ole -olidine -ole -olan6 -ine perhydro -in -ane/-an7 -epine perhydro -epin -epan8 -ocine perhydro -ocin -ocan9 -ecine perhydro -onin -onan


Suffix and Prefix


NH O S

1H-Pyrrole

NH

Pyrroline

NH

2, 3-Dihydro-1H-pyrroline

Pyrrolidine

OFurole

2, 3-Dihydrofuran

Furan Thiophene

S

2, 3-Dihydrothiophene

O

Tetrahydrofuran

S

Tetrahydrothiophene

Rings with Two Heteroatoms


Heteroatom present is indicated by prefixing respective phrases

Nitrogen: Aza-

Oxygen: Oxa- Sulphur: Thia-

1H-Pyrazole Pyridazine

NNH

NN

N

S

Thiazole

N

O

Oxazole


Heteroatoms appearing higher, and with lower atomic number in the periodictable is given precedence

Precedence of Heteroatoms

B C N O F

Al Si P S Cl

N

O

NH

NH

O

Oxazole

N

N

O

1, 3, 5-Oxadiazine

1, 3, 5-2H-Oxadiazine

1, 3, 5-Oxadiazinane

O

S

N

6H-1, 3, 5-Oxathiazine

Numbering?

H?


Precedence for Numbering of HeteroatomsHeteroatoms appearing lower in a group in the periodic table is given lowernumbering, and the sequence is followed

O32

4

S1

N56

N3

4

2 5

O1

3 4

N2

5

S1

2

3

O1

O4

6

5

3

2

O4

S1

5

6

2

3

O1

NH4

6

5

Dioxane

1, 4-Oxathiane

Morpholine


Fused Rings

N

NH

O

1, 4-Dihydrobenzo[h]isoquinoline Hexahydro-2H –furo[2, 3-b]pyrrole

Hexahydro-2H –thieno[2, 3-b]pyrrole

NH

S


Rules

Heterocyclic ring is chosen as parent compound

More than one heterocyclic ring is present, then nitrogen containing ring is chosen as parent compound

Ring containing nitrogen is preferred; if nitrogen is absent then preference isgiven to higher atom in a group in periodic table.

Lower number to atom with lower atomic number

Name of the fused ring is prefixed to name of parent ring with ‘o’ in-between

Largest possible component is chosen

Larger number of ring are placed horizontal and then less number ring go toright corner and then numbering is done in clockwise direction


Isomeric heterocyclic compounds are differentiated by splitting the rings after deciding the precedence

Rings are numbered individually

Faces are marked with lower-case alphabets, low numbered to get lowest alphabet

Rings are then fused

Numbering is done over the re-fused rings


NH

S

hexahydro-2H-thieno[2,3-b]pyrrole

NH

S

hexahydro-2H-thieno[2,3-c]pyrrole

NH

Shexahydro-2H-thieno[3,2-b]pyrrole

NN

O

5H-pyrido[2,3-d][1,2]oxazine


Department of Pharmaceutical Chemistry

P. G. Section

Laboratory Tour

Acknowledgements

Fraternity of Teachers


Prof. S. R. Tambe

Staff of MGV’s College of Pharmacy, Malegoan

Nomenclature

Education

Transcript of Nomenclature