Polymer Mixture Deconvolution via NMR spectroscopy and … · 2020-03-16 · and ACD/Labs database...
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Chlorinated Paraffin Mixture Deconvolution via NMR spectroscopy and ACD/Labs database Ronald Soong & Andre Simpson University of Toronto Scarborough
Transcript of Polymer Mixture Deconvolution via NMR spectroscopy and … · 2020-03-16 · and ACD/Labs database...
Chlorinated Paraffin Mixture Deconvolution via NMR spectroscopy and ACD/Labs databaseRonald Soong & Andre Simpson
University of Toronto Scarborough
OUTLINE
• Introduction• NMR spectroscopy• Database construction• Database searches• Result presentation• Final Remarks
Polymer Mixture
Introduction
Chlorinated Paraffins
• Short-chain CPs are classified as persistent and their physical properties (octanol-water partition coefficient (logKOW) 4.4–8, depending on the chlorination degree) imply a high potential for bioaccumulation. Furthermore, SCCPs are classified as toxic to aquatic organisms, and carcinogenic to rats and mice.
NMR spectroscopy
Chemical Shift (ppm)6 5 4 3
Chemical Shift (ppm)6 5 4 3
C14 CPs C14 CPs C14 CPs C14 CPs C14 CPs
(a)
NMR spectroscopy
of Mixture Profiling
Chemical Shift (ppm)6 5 4 3
Chemical Shift (ppm)6 5 4 3
C14 CPs C14 CPs C14 CPs C14 CPs C14 CPs
(a)
Construction of Database
8 3 2 5 6 9 10 11 12 13 14 15 17 18H8a
H8b
H8c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
Cl7
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
12 4 3 2 6 7 8 9 10 13 14 15 17 18H12a
H12b
H12c
H4a
Cl5
H3a
H3b
Cl1
H2a
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
Cl11
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
4 3 2 6 7 9 10 12 13 14 15 16 17 18H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
Cl8
H9a
H9b
H10a
Cl11
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H18a
H18b
H18c
4 3 2 6 7 8 9 11 12 13 14 15 17 18H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
Cl10
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
9 8 7 6 2 3 4 11 12 13 14 15 17 18H9a
Cl10
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
4 3 2 6 7 9 10 11 12 13 14 15 16 18H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
Cl8
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
Cl17
H18a
H18b
H18c
15 14 13 12 11 10 4 3 2 6 7 8 17 18H15a
Cl16
H15b
H14a
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
Cl9
H17a
H17b
H18a
H18b
H18c
15 14 13 12 11 10 3 2 5 6 7 8 17 18H15a
Cl16
H15b
H14a
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H17a
H17b
H18a
H18b
H18c
9 8 7 6 5 2 3 11 12 13 14 15 17 18H9a
Cl10
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
8 7 6 5 2 3 10 11 12 13 14 15 17 18H8a
Cl9
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
10 3 2 5 6 7 8 11 12 13 14 15 16 18H10a
H10b
H10c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
Cl17
H18a
H18b
H18c
16 15 7 6 2 3 4 9 10 11 12 13 17 18H16a
H16b
H16c
H15a
H15b
H7a
Cl8
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H17a
H17b
H18a
H18b
H18c
16 7 6 2 3 4 9 10 11 12 13 14 17 18H16a
H16b
H16c
H7a
Cl8
H6a
H6b
Cl1
H2a
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H17a
H17b
H18a
H18b
H18c
5 4 3 2 7 8 9 11 12 13 14 15 17 18H5a
Cl6
H5b
H4a
H4b
H3a
H3b
Cl1
H2a
H7a
H7b
H8a
H8b
H9a
Cl10
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
18 17 15 14 8 7 6 5 2 3 10 11 12 13H18a
H18b
H18c
H17a
H17b
H15a
Cl16
H14a
H14b
H8a
Cl9
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H13c
17 16 15 11 10 9 8 7 2 3 4 5 13 14H17a
Cl18
H17b
H16a
H16b
H15a
H15b
Cl12
H11a
H10a
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
Cl6
H13a
H13b
H14a
H14b
H14c
18 16 15 8 7 6 2 3 4 10 11 12 13 14H18a
H18b
H18c
H16a
Cl17
H15a
H15b
Cl9
H8a
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
18 17 10 9 4 3 2 6 7 12 13 14 15 16H18a
H18b
H18c
H17a
H17b
H10a
Cl11
H9a
H9b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
Cl8
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
17 16 9 8 7 6 5 4 2 11 12 13 14 15H17a
Cl18
H17b
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
7 6 5 4 2 9 10 11 12 13 14 15 17 18H7a
Cl8
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
16 15 7 6 5 4 2 9 10 11 12 13 17 18H16a
H16b
H16c
H15a
H15b
H7a
Cl8
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H17a
H17b
H18a
H18b
H18c
8 7 6 5 4 2 10 11 12 13 14 15 17 18H8a
Cl9
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
17 16 8 7 6 5 4 2 10 11 12 13 14 15H17a
Cl18
H17b
H16a
H16b
H8a
Cl9
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
18 16 15 7 6 5 4 2 9 10 11 12 13 14H18a
H18b
H18c
H16a
Cl17
H15a
H15b
Cl8
H7a
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
10 2 4 5 6 7 8 11 12 13 14 15 17 18H10a
H10b
H10c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
18 16 15 14 7 6 5 4 2 9 10 11 12 13H18a
H18b
H18c
H16a
Cl17
H15a
H15b
H14a
H14b
H7a
Cl8
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H13c
10 2 4 5 6 7 8 11 12 14 15 16 17 18H10a
H10b
H10c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
Cl13
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H18a
H18b
H18c
15 14 13 12 11 10 2 4 5 6 7 8 17 18H15a
Cl16
H15b
H14a
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H17a
H17b
H18a
H18b
H18c
17 16 15 8 7 6 5 4 2 10 11 12 13 14H17a
Cl18
H17b
H16a
H16b
H15a
H15b
Cl9
H8a
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
18 8 7 6 5 4 2 10 11 12 13 14 15 16H18a
H18b
H18c
Cl9
Cl17
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
18 10 9 8 7 6 5 4 2 12 13 14 15 16H18a
H18b
H18c
Cl11
Cl17
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
7 6 5 4 3 2 9 10 11 12 13 14 16 17H7a
Cl8
H7b
H6a
H6b
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
15 14 6 5 4 3 2 8 9 10 11 12 16 17H15a
H15b
H15c
H14a
H14b
H6a
Cl7
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
Cl13
H16a
H16b
H17a
H17b
H17c
17 8 7 6 2 3 4 10 11 12 13 14 15 16H17a
H17b
H17c
H8a
Cl9
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
8 7 6 5 4 3 2 10 11 12 13 14 15 17H8a
Cl9
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H17c
5 4 3 2 7 8 9 10 11 13 14 15 16 17H5a
Cl6
H5b
H4a
H4b
H3a
H3b
Cl1
H2a
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
Cl12
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
15 5 4 3 2 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
H5a
Cl6
H4a
H4b
H3a
H3b
H2a
Cl1
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
9 8 7 6 2 3 4 11 12 13 14 15 16 17H9a
Cl10
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
10 9 8 7 6 2 3 4 12 13 14 15 16 17H10a
Cl11
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
5 4 3 2 7 8 9 10 11 12 13 14 16 17H5a
Cl6
H5b
H4a
H4b
H3a
H3b
Cl1
H2a
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
15 14 4 3 2 6 7 8 9 10 11 12 16 17H15a
H15b
H15c
H14a
H14b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
Cl13
H16a
H16b
H17a
H17b
H17c
17 16 15 14 7 6 2 3 4 9 10 11 12 13H17a
H17b
H17c
H16a
H16b
H15a
H15b
H14a
H14b
H7a
Cl8
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H13c
4 3 2 6 7 8 9 10 11 12 13 14 16 17H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
10 3 2 5 6 7 8 11 12 13 14 15 16 17H10a
H10b
H10c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 10 9 8 7 6 2 3 4 12 13 14 15 16H17a
H17b
H17c
H10a
Cl11
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
15 4 3 2 6 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
H4a
Cl5
H3a
H3b
Cl1
H2a
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
4 3 2 6 7 8 9 11 12 13 14 15 16 17H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
Cl10
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 16 9 8 7 2 3 4 5 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
Cl6
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 9 8 7 6 2 3 4 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
11 10 9 8 7 6 2 3 4 13 14 15 16 17H11a
Cl12
H11b
H10a
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
6 5 4 3 2 8 9 10 11 12 13 14 16 17H6a
Cl7
H6b
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
12 11 4 3 2 6 7 8 9 13 14 15 16 17H12a
H12b
H12c
H11a
H11b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
Cl10
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
14 13 12 11 10 9 2 3 4 5 6 7 16 17H14a
Cl15
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
H5b
H6a
H6b
H7a
Cl8
H16a
H16b
H17a
H17b
H17c
17 16 8 7 6 2 3 4 10 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H8a
Cl9
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 13 12 11 10 9 8 2 3 4 5 6 15 16H17a
H17b
H17c
H13a
Cl14
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H8a
H8b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
H5b
H6a
Cl7
H15a
H15b
H16a
H16b
H16c
15 3 2 5 6 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
13 12 4 3 2 6 7 8 9 10 14 15 16 17H13a
H13b
H13c
H12a
H12b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
Cl11
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 16 7 6 2 3 4 9 10 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H7a
Cl8
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 10 9 8 7 6 5 2 3 12 13 14 15H17a
H17b
H17c
H16a
H16b
H10a
Cl11
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 10 9 8 7 6 2 3 4 12 13 14 15H17a
H17b
H17c
H16a
H16b
H10a
Cl11
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 13 12 11 10 9 8 7 6 2 3 4 15 16H17a
H17b
H17c
H13a
Cl14
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H15a
H15b
H16a
H16b
H16c
17 16 15 8 7 6 5 4 2 10 11 12 13 14H17a
H17b
H17c
H16a
H16b
H15a
H15b
Cl9
H8a
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
15 2 4 5 6 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
10 2 4 5 6 7 8 11 12 13 14 15 16 17H10a
H10b
H10c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 13 12 11 10 9 2 3 4 5 6 7 15 16H17a
H17b
H17c
H13a
Cl14
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
H5b
H6a
H6b
H7a
Cl8
H15a
H15b
H16a
H16b
H16c
17 16 9 8 7 6 5 4 2 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 8 7 6 5 4 2 10 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H8a
Cl9
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
All possible structural permutation based on linear polymer backbone Generate 13C NMR spectra of all possible structure
Search for the top 1000 hits based on an experimental 13C NMR spectrum of a particular
polymer mixture
From the top 1000 hit, we generate a 2D HSQC from the top 100
8 6 4 2 0
0
20
40
60
80
100
120
140
8 6 4 2
0
20
40
60
80
100
120
140
CL14CL40
We matched the top 100 with the experimental HSQC spectrum
Full spectral assignment
Structural Permutation
1 2 3 4 5 6 7 8 9
P1 1 1 1
P2 2 1
P3
P4 1 1 1
P5 3Over 100K Entries and 3 days of computation time for each molecular formula
Chemical Shift (ppm)64 56 48 40 32
Chemical Shift (ppm)66 64 62 60
Chemical Shift (ppm)6 5 4 3
Chemical Shift (ppm)6 5 4 3
C14 CPs C14 CPs C14 CPs C14 CPs C14 CPs
(a)
What we do on those 3 days?
Chlorinated Paraffin Peaks
ACD/Labs Simulation Workflow
8 3 2 5 6 9 10 11 12 13 14 15 17 18H8a
H8b
H8c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
Cl7
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
12 4 3 2 6 7 8 9 10 13 14 15 17 18H12a
H12b
H12c
H4a
Cl5
H3a
H3b
Cl1
H2a
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
Cl11
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
4 3 2 6 7 9 10 12 13 14 15 16 17 18H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
Cl8
H9a
H9b
H10a
Cl11
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H18a
H18b
H18c
4 3 2 6 7 8 9 11 12 13 14 15 17 18H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
Cl10
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
9 8 7 6 2 3 4 11 12 13 14 15 17 18H9a
Cl10
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
4 3 2 6 7 9 10 11 12 13 14 15 16 18H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
Cl8
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
Cl17
H18a
H18b
H18c
15 14 13 12 11 10 4 3 2 6 7 8 17 18H15a
Cl16
H15b
H14a
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
Cl9
H17a
H17b
H18a
H18b
H18c
15 14 13 12 11 10 3 2 5 6 7 8 17 18H15a
Cl16
H15b
H14a
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H17a
H17b
H18a
H18b
H18c
9 8 7 6 5 2 3 11 12 13 14 15 17 18H9a
Cl10
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
8 7 6 5 2 3 10 11 12 13 14 15 17 18H8a
Cl9
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
10 3 2 5 6 7 8 11 12 13 14 15 16 18H10a
H10b
H10c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
Cl17
H18a
H18b
H18c
16 15 7 6 2 3 4 9 10 11 12 13 17 18H16a
H16b
H16c
H15a
H15b
H7a
Cl8
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H17a
H17b
H18a
H18b
H18c
16 7 6 2 3 4 9 10 11 12 13 14 17 18H16a
H16b
H16c
H7a
Cl8
H6a
H6b
Cl1
H2a
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H17a
H17b
H18a
H18b
H18c
5 4 3 2 7 8 9 11 12 13 14 15 17 18H5a
Cl6
H5b
H4a
H4b
H3a
H3b
Cl1
H2a
H7a
H7b
H8a
H8b
H9a
Cl10
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
18 17 15 14 8 7 6 5 2 3 10 11 12 13H18a
H18b
H18c
H17a
H17b
H15a
Cl16
H14a
H14b
H8a
Cl9
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H13c
17 16 15 11 10 9 8 7 2 3 4 5 13 14H17a
Cl18
H17b
H16a
H16b
H15a
H15b
Cl12
H11a
H10a
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
Cl6
H13a
H13b
H14a
H14b
H14c
18 16 15 8 7 6 2 3 4 10 11 12 13 14H18a
H18b
H18c
H16a
Cl17
H15a
H15b
Cl9
H8a
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
18 17 10 9 4 3 2 6 7 12 13 14 15 16H18a
H18b
H18c
H17a
H17b
H10a
Cl11
H9a
H9b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
Cl8
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
17 16 9 8 7 6 5 4 2 11 12 13 14 15H17a
Cl18
H17b
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
7 6 5 4 2 9 10 11 12 13 14 15 17 18H7a
Cl8
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
16 15 7 6 5 4 2 9 10 11 12 13 17 18H16a
H16b
H16c
H15a
H15b
H7a
Cl8
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H17a
H17b
H18a
H18b
H18c
8 7 6 5 4 2 10 11 12 13 14 15 17 18H8a
Cl9
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
17 16 8 7 6 5 4 2 10 11 12 13 14 15H17a
Cl18
H17b
H16a
H16b
H8a
Cl9
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
18 16 15 7 6 5 4 2 9 10 11 12 13 14H18a
H18b
H18c
H16a
Cl17
H15a
H15b
Cl8
H7a
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
10 2 4 5 6 7 8 11 12 13 14 15 17 18H10a
H10b
H10c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H18a
H18b
H18c
18 16 15 14 7 6 5 4 2 9 10 11 12 13H18a
H18b
H18c
H16a
Cl17
H15a
H15b
H14a
H14b
H7a
Cl8
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H13c
10 2 4 5 6 7 8 11 12 14 15 16 17 18H10a
H10b
H10c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
Cl13
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H18a
H18b
H18c
15 14 13 12 11 10 2 4 5 6 7 8 17 18H15a
Cl16
H15b
H14a
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H17a
H17b
H18a
H18b
H18c
17 16 15 8 7 6 5 4 2 10 11 12 13 14H17a
Cl18
H17b
H16a
H16b
H15a
H15b
Cl9
H8a
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
18 8 7 6 5 4 2 10 11 12 13 14 15 16H18a
H18b
H18c
Cl9
Cl17
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
18 10 9 8 7 6 5 4 2 12 13 14 15 16H18a
H18b
H18c
Cl11
Cl17
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
7 6 5 4 3 2 9 10 11 12 13 14 16 17H7a
Cl8
H7b
H6a
H6b
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
15 14 6 5 4 3 2 8 9 10 11 12 16 17H15a
H15b
H15c
H14a
H14b
H6a
Cl7
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
Cl13
H16a
H16b
H17a
H17b
H17c
17 8 7 6 2 3 4 10 11 12 13 14 15 16H17a
H17b
H17c
H8a
Cl9
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
8 7 6 5 4 3 2 10 11 12 13 14 15 17H8a
Cl9
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
Cl16
H17a
H17b
H17c
5 4 3 2 7 8 9 10 11 13 14 15 16 17H5a
Cl6
H5b
H4a
H4b
H3a
H3b
Cl1
H2a
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
Cl12
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
15 5 4 3 2 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
H5a
Cl6
H4a
H4b
H3a
H3b
H2a
Cl1
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
9 8 7 6 2 3 4 11 12 13 14 15 16 17H9a
Cl10
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
10 9 8 7 6 2 3 4 12 13 14 15 16 17H10a
Cl11
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
5 4 3 2 7 8 9 10 11 12 13 14 16 17H5a
Cl6
H5b
H4a
H4b
H3a
H3b
Cl1
H2a
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
15 14 4 3 2 6 7 8 9 10 11 12 16 17H15a
H15b
H15c
H14a
H14b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
Cl13
H16a
H16b
H17a
H17b
H17c
17 16 15 14 7 6 2 3 4 9 10 11 12 13H17a
H17b
H17c
H16a
H16b
H15a
H15b
H14a
H14b
H7a
Cl8
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H13c
4 3 2 6 7 8 9 10 11 12 13 14 16 17H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
10 3 2 5 6 7 8 11 12 13 14 15 16 17H10a
H10b
H10c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 10 9 8 7 6 2 3 4 12 13 14 15 16H17a
H17b
H17c
H10a
Cl11
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H16c
15 4 3 2 6 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
H4a
Cl5
H3a
H3b
Cl1
H2a
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
4 3 2 6 7 8 9 11 12 13 14 15 16 17H4a
Cl5
H4b
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
Cl10
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 16 9 8 7 2 3 4 5 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
Cl6
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 9 8 7 6 2 3 4 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
11 10 9 8 7 6 2 3 4 13 14 15 16 17H11a
Cl12
H11b
H10a
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
6 5 4 3 2 8 9 10 11 12 13 14 16 17H6a
Cl7
H6b
H5a
H5b
H4a
H4b
H3a
H3b
H2a
Cl1
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
Cl15
H16a
H16b
H17a
H17b
H17c
12 11 4 3 2 6 7 8 9 13 14 15 16 17H12a
H12b
H12c
H11a
H11b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
Cl10
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
14 13 12 11 10 9 2 3 4 5 6 7 16 17H14a
Cl15
H14b
H13a
H13b
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
H5b
H6a
H6b
H7a
Cl8
H16a
H16b
H17a
H17b
H17c
17 16 8 7 6 2 3 4 10 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H8a
Cl9
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 13 12 11 10 9 8 2 3 4 5 6 15 16H17a
H17b
H17c
H13a
Cl14
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H8a
H8b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
H5b
H6a
Cl7
H15a
H15b
H16a
H16b
H16c
15 3 2 5 6 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
H3a
Cl4
H2a
Cl1
H5a
H5b
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
13 12 4 3 2 6 7 8 9 10 14 15 16 17H13a
H13b
H13c
H12a
H12b
H4a
Cl5
H3a
H3b
H2a
Cl1
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
Cl11
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 16 7 6 2 3 4 9 10 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H7a
Cl8
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 10 9 8 7 6 5 2 3 12 13 14 15H17a
H17b
H17c
H16a
H16b
H10a
Cl11
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H2a
Cl1
H3a
Cl4
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 10 9 8 7 6 2 3 4 12 13 14 15H17a
H17b
H17c
H16a
H16b
H10a
Cl11
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 13 12 11 10 9 8 7 6 2 3 4 15 16H17a
H17b
H17c
H13a
Cl14
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H8a
H8b
H7a
H7b
H6a
H6b
H2a
Cl1
H3a
H3b
H4a
Cl5
H15a
H15b
H16a
H16b
H16c
17 16 15 8 7 6 5 4 2 10 11 12 13 14H17a
H17b
H17c
H16a
H16b
H15a
H15b
Cl9
H8a
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H14c
15 2 4 5 6 7 8 9 10 11 12 13 16 17H15a
H15b
H15c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
H8b
H9a
H9b
H10a
H10b
H11a
H11b
H12a
H12b
H13a
Cl14
H16a
H16b
H17a
H17b
H17c
10 2 4 5 6 7 8 11 12 13 14 15 16 17H10a
H10b
H10c
Cl1
Cl3
H4a
H4b
H5a
H5b
H6a
H6b
H7a
H7b
H8a
Cl9
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H16a
H16b
H17a
H17b
H17c
17 13 12 11 10 9 2 3 4 5 6 7 15 16H17a
H17b
H17c
H13a
Cl14
H12a
H12b
H11a
H11b
H10a
H10b
H9a
H9b
H2a
Cl1
H3a
H3b
H4a
H4b
H5a
H5b
H6a
H6b
H7a
Cl8
H15a
H15b
H16a
H16b
H16c
17 16 9 8 7 6 5 4 2 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H9a
Cl10
H8a
H8b
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
17 16 8 7 6 5 4 2 10 11 12 13 14 15H17a
H17b
H17c
H16a
H16b
H8a
Cl9
H7a
H7b
H6a
H6b
H5a
H5b
H4a
H4b
Cl1
Cl3
H10a
H10b
H11a
H11b
H12a
H12b
H13a
H13b
H14a
H14b
H15a
H15b
H15c
Polymers IsomersDatabase
We can break the region down into fragment chartsThis is an example for the C14CL(60%) mixture. How to interpret key32 = terminal with 3,2 proton so CH3-CH2- -020- = midchain with -0-2-0- protons so -Cl2-CH2-Cl2- etc.
We matched the top 100 with the experimental HSQC spectrum
Putting all the pieces together
By including all the 2-3 BOND 1H-13C
correlations (C14CL(60%))
assignment of all regions become quite
unambiguous.
HMBC NMR Spectrum
How to interpret keyT32 = terminal with 3,2 proton so CH3-CH2-M020 = midchain with 0-2-0 protons so -Cl2-CH2-Cl2-
The Answer: Substitution Heat Maps: Distribution of Exact Isomeric Structures
Both the top 1000 and top 100 structures based on NMR matches can be used generalize the structures that are present.
An easy way we found to do this is essentially a structural “heat map”.
The top row represents the % probability of a chlorine at that position in the chain CLCH. The bottom row shows the % probability of a second CL opposite (i.e. CL2 unit).
The heat maps from top 100 structures will give you an idea of the chlorination in the most abundant structures
The top 1000 more of an idea as to the substitutions over the wider range of structures present.
C14
Cl(4
0)C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C14
Cl(4
0)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C1b
12% 23% 26% 53% 27% 26% 29% 29% 29% 29% 26% 27% 53% 26% 23% 12%
C14b C
1b 0%
19% 16% 38% 8% 16% 20% 26% 26% 20% 16% 8% 38% 16% 19% 0%
C14b8% 11% 17% 10% 9% 11% 11% 11% 11% 9% 10% 17% 11% 8% 0% 4% 0% 0% 1% 4% 4% 4% 4% 1% 0% 0% 4% 0%
C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c
C14
Cl(4
5)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C14
Cl(4
5)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C1b 8%
16% 19% 71% 37% 47% 45% 34% 34% 45% 47% 37% 71% 19% 16% 8%
C14b C
1b 6%
18% 21% 61% 17% 29% 40% 27% 27% 40% 29% 17% 61% 21% 18% 6%
C14b6% 8% 13% 6% 11% 14% 13% 13% 14% 11% 6% 13% 8% 6% 6% 8% 3% 0% 4% 7% 11% 11% 7% 4% 0% 3% 8% 6%
C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c
C14
Cl(5
0)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C14
Cl(5
0)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C1b
10% 24% 23% 78% 34% 43% 46% 30% 30% 46% 43% 34% 78% 23% 24% 10%
C14b C
1b 4%
18% 26% 72% 14% 24% 45% 35% 35% 45% 24% 14% 72% 26% 18% 4%
C14b6% 9% 12% 9% 11% 11% 7% 7% 11% 11% 9% 12% 9% 6% 4% 10% 4% 0% 1% 4% 2% 2% 4% 1% 0% 4% 10% 4%
C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c
C14
Cl(5
5)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C14
Cl(5
5)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C1b
19% 51% 52% 57% 30% 34% 33% 38% 38% 33% 34% 30% 57% 52% 51% 19%
C14b C
1b 4%
27% 45% 57% 23% 26% 26% 50% 50% 26% 26% 23% 57% 45% 27% 4%
C14b11% 15% 14% 7% 10% 8% 9% 9% 8% 10% 7% 14% 15% 11% 4% 13% 5% 0% 4% 3% 8% 8% 3% 4% 0% 5% 13% 4%
C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c
C14
Cl(6
0)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C14
Cl(6
0)
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C1b
16% 66% 55% 62% 31% 45% 39% 44% 44% 39% 45% 31% 62% 55% 66% 16%
C14b C
1b
10% 78% 55% 65% 33% 40% 45% 47% 47% 45% 40% 33% 65% 55% 78% 10%
C14b10% 10% 8% 4% 9% 5% 11% 11% 5% 9% 4% 8% 10% 10% 10% 11% 3% 2% 5% 9% 9% 9% 9% 5% 2% 3% 11% 10%
C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c
Aver
aged
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
Aver
aged
C1a C2a C3a C4a C5a C6a C7a C8a C9a C10a C11a C12a C13a C14a
C1b
13% 36% 35% 64% 32% 39% 38% 35% 35% 38% 39% 32% 64% 35% 36% 13%
C14b C
1b 5%
32% 33% 58% 19% 27% 35% 37% 37% 35% 27% 19% 58% 33% 32% 5%
C14b8% 10% 13% 7% 10% 10% 10% 10% 10% 10% 7% 13% 10% 8% 5% 9% 3% 0% 3% 5% 7% 7% 5% 3% 0% 3% 9% 5%
C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c C1c C2b C3b C4b C5b C6b C7b C8b C9b C10b C11b C12b C13b C14c
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Conclusion• We have successful build a isomeric database• Using this database, we have characterized the isomeric mixture• To characterize the mixture, we use a heat map approaching illustrating
the probability of finding a chlorine in a particular position of a linear chlorinated paraffin.
• The combine approach of NMR and database allows for the characterization of an isomer chlorinated mixture
