Standard Article

Thermochemistry of Olefins, Carbonyl Compounds and Imines

Double-bonded Functional Groups (1997)

  1. Suzanne W. Slayden1,
  2. Joel F. Liebman2

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0128

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Slayden, S. W. and Liebman, J. F. 2009. Thermochemistry of Olefins, Carbonyl Compounds and Imines. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    George Mason University, Department of Chemistry, Fairfax, Virginia, USA

  2. 2

    University of Maryland Baltimore County, Department of Chemistry and Biochemistry, Baltimore, Maryland, USA

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction: Scope and Definitions
  • 2
    Acyclic Olefins
  • 3
    Cyclic Olefins with a [BOND]CH[DOUBLE BOND]CH[BOND] Group
  • 4
    Exo- vs Endo-Cyclic Double Bonds
  • 5
    Bredt's Rule, Bridgehead Olefins and Cyclic Species with a A >C[DOUBLE BOND]CH[BOND] Olefinic Linkage
  • 6
    Cyclic Olefins Containing a Tetrasubstituted Double Bond
  • 7
    Olefins with Aromatic Substituents
  • 8
    Acyclic Aldehydes and Ketones
  • 9
    Alicyclic Ketones
  • 10
    Carbonyl Compounds with Aryl Substituents
  • 11
    Polycarbonyl Compounds
  • 12
    Imines

Keywords:

  • olefin, carbonyl compounds and imine thermochemistry;
  • acyclic olefins;
  • alkene data assessment;
  • cyclic olefins with a–CH[BOND]CH–group;
  • Trans-Cycloalkenes;
  • exo- vs endo-cyclic double bonds;
  • isomeric methylcycloalkenes and methylenecycloalkanes;
  • isomeric ethylcycloalkenes, ethylidenecycloalkanes and vinylcycloalkanes

Featured Compounds

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  1. 1 - 122
Compound 1
Molecular Weight:Not Available
Molecular Formula:(CH2)nC2H2
InChIKey:OOXWYYGXTJLWHA-UHFFFAOYSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:(CH2)nC2H4
InChIKey:LVZWSLJZHVFIQJ-UHFFFAOYSA-N
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Compound 4
Molecular Weight:Not Available
Molecular Formula:(CH2)nC5H6
InChIKey:BAOZQZPGQWXJOW-UHFFFAOYSA-N
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Compound 5
Molecular Weight:Not Available
Molecular Formula:(CH2)nC4H4
InChIKey:CGKPQMCLTLUAOW-UHFFFAOYSA-N
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Compound 6a
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:WJSPKNSMGLBHBW-UHFFFAOYSA-N
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Compound 23c
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:LMULYBMQCQUKHQ-UHFFFAOYSA-N
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Compound 6b
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:JBFDZEJAJZJORO-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:Not Available
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Compound 7b
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:UVJHQYIOXKWHFD-UHFFFAOYSA-N
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Compound 8
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:JBFDZEJAJZJORO-ULUSZKPHSA-N
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Compound 9
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H8
InChIKey:JFNLZVQOOSMTJK-UHFFFAOYSA-N
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Compound 10
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:KEHFJHPSOFFXBO-UHFFFAOYSA-N
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Compound 11
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:VMQPMGHYRISRHO-UHFFFAOYSA-N
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Compound 12
Molecular Weight:134.2182
Molecular Formula:C10H14
InChIKey:VVQPGPGAEHQIBD-UHFFFAOYSA-N
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Compound 13a
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:XBFJAVXCNXDMBH-GEDKWGBFSA-N
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Compound 13b
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:XBFJAVXCNXDMBH-VDUKMOIZSA-N
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Compound 13c
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:XBFJAVXCNXDMBH-VDUKMOIZSA-N
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Compound 14
Molecular Weight:212.33
Molecular Formula:C16H20
InChIKey:KGSHKEGGGVMYNT-UHFFFAOYSA-N
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Compound 15
Molecular Weight:134.2182
Molecular Formula:C10H14
InChIKey:HANKSFAYJLDDKP-UHFFFAOYSA-N
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Compound 16a
Molecular Weight:200.3193
Molecular Formula:C15H20
InChIKey:LIXRTJVYXUPFLI-LIVOHKEASA-N
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Compound 16b
Molecular Weight:200.3193
Molecular Formula:C15H20
InChIKey:LIXRTJVYXUPFLI-UHFFFAOYSA-N
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Compound 17
Molecular Weight:356.6276
Molecular Formula:C26H44
InChIKey:WYAQFFKTQCBZSW-UHFFFAOYSA-N
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Compound 18a
Molecular Weight:Not Available
Molecular Formula:(CH2)nC3H4
InChIKey:SHDPRTQPPWIEJG-UHFFFAOYSA-N
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Compound 18b
Molecular Weight:Not Available
Molecular Formula:(CH2)nC3H4
InChIKey:XSGHLZBESSREDT-UHFFFAOYSA-N
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Compound 19a
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:HTENSGOZPYEMCG-UHFFFAOYSA-N
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Compound 19b
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:AJQVASAUQUTVJK-UHFFFAOYSA-N
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Compound 45a
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:AJQVASAUQUTVJK-UHFFFAOYSA-N
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Compound 20b
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:Not Available
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Compound 20a
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:GRWFGVWFFZKLTI-UHFFFAOYSA-N
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Compound 21a
Molecular Weight:Not Available
Molecular Formula:(CH2)nC4H6
InChIKey:QHFUTZLUZYEBIN-UHFFFAOYSA-N
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Compound 21b
Molecular Weight:Not Available
Molecular Formula:(CH2)nC4H6
InChIKey:ZIFNDRXSSPCNID-UHFFFAOYSA-N
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Compound 21c
Molecular Weight:Not Available
Molecular Formula:(CH2)nC4H6
InChIKey:YIWFBNMYFYINAD-UHFFFAOYSA-N
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Compound 22a
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:SIVKZPBURVINMX-UHFFFAOYSA-N
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Compound 22b
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:BFHUIVOGLJUQID-UHFFFAOYSA-N
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Compound 22c
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:NCQNMEMRZWQKGX-UHFFFAOYSA-N
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Compound 22d
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:CEVDPSDZXGCLEI-UHFFFAOYSA-N
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Compound 23a
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:PKCMTAKKGOCYFF-UHFFFAOYSA-N
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Compound 23b
Molecular Weight:93.1458
Molecular Formula:C7H10
InChIKey:FLQIRABUTHSITP-UHFFFAOYSA-N
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Compound 24
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:QWKHRBFLFYXNDY-UHFFFAOYSA-N
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Compound 25
Molecular Weight:Not Available
Molecular Formula:(CH2)m(CH2)nC2
InChIKey:JTVNFJINIGKHAV-UHFFFAOYSA-N
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Compound 26
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:GKYMZAJXGNOYBX-UHFFFAOYSA-N
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Compound 27a
Molecular Weight:102.1332
Molecular Formula:C8H6
InChIKey:WUXSWGVAYSJTJS-UHFFFAOYSA-N
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Compound 27b
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:TXWRERCHRDBNLG-UHFFFAOYSA-N
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Compound 28
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:XACJYLQNZRRIJA-UHFFFAOYSA-N
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Compound 29
Molecular Weight:260.3728
Molecular Formula:C20H20
InChIKey:OOHPORRAEMMMCX-UHFFFAOYSA-N
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Compound 30a
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound 30b
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-VAWYXSNFSA-N
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Compound 30c
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:ZMYIIHDQURVDRB-UHFFFAOYSA-N
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Compound 30d
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-QXMHVHEDSA-N
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Compound 31a
Molecular Weight:256.341
Molecular Formula:C20H16
InChIKey:Not Available
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Compound 31b
Molecular Weight:332.437
Molecular Formula:C26H20
InChIKey:JLZUZNKTTIRERF-UHFFFAOYSA-N
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Compound 32
Molecular Weight:208.2982
Molecular Formula:C16H16
InChIKey:KINZBJFIDFZQCB-VAWYXSNFSA-N
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Compound 33a
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:XYLMUPLGERFSHI-UHFFFAOYSA-N
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Compound 33b
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:QROGIFZRVHSFLM-QHHAFSJGSA-N
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Compound 33c
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:QROGIFZRVHSFLM-KXFIGUGUSA-N
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Compound 33d
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:BTOVVHWKPVSLBI-UHFFFAOYSA-N
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Compound 34
Molecular Weight:116.1598
Molecular Formula:C9H8
InChIKey:YBYIRNPNPLQARY-UHFFFAOYSA-N
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Compound 35
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:Not Available
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Compound 36
Molecular Weight:152.1919
Molecular Formula:C12H8
InChIKey:HXGDTGSAIMULJN-UHFFFAOYSA-N
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Compound 50a
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:CXWXQJXEFPUFDZ-UHFFFAOYSA-N
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Compound 37
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:WCMSFBRREKZZFL-UHFFFAOYSA-N
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Compound 61
Molecular Weight:Not Available
Molecular Formula:(C2H2O)nC2H6
InChIKey:ZWEHNKRNPOVVGH-UHFFFAOYSA-N
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Compound 38
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39a
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:KPMKEVXVVHNIEY-UHFFFAOYSA-N
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Compound 39b
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:ZESXVLLAIXOYKB-UHFFFAOYSA-N
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Compound 40a
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:VEPYQCZRVLNDBC-UHFFFAOYSA-N
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Compound 40b
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:NZTVVUIIJPWANB-UHFFFAOYSA-N
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Compound 40c
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:NZTVVUIIJPWANB-MLWJPKLSSA-N
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Compound 41a
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:HAMUKWWZXAKCAU-UHFFFAOYSA-N
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Compound 41b
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:HAMUKWWZXAKCAU-GVHYBUMESA-N
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Compound 41c
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:SKTMMSQPXGWCAP-UHFFFAOYSA-N
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Compound 42
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:Not Available
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Compound 43
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:WOLSPKYGHOUIFM-UHFFFAOYSA-N
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 45b
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:JSASFGPUXQDHEC-UHFFFAOYSA-N
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Compound 46
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:BOXGGSPOSRTPTH-UHFFFAOYSA-N
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Compound 48
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:DSSYKIVIOFKYAU-UHFFFAOYSA-N
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Compound 47
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:AMBOSHXMUMOHBF-UHFFFAOYSA-N
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Compound 49a
Molecular Weight:260.4574
Molecular Formula:C19H32
InChIKey:QZLYKIGBANMMBK-RLHPCVIISA-N
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Compound 49b
Molecular Weight:288.4244
Molecular Formula:C19H28O2
InChIKey:RAJWOBJTTGJROA-PLFHKJOISA-N
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Compound 50b
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:XHLHPRDBBAGVEG-UHFFFAOYSA-N
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Compound 51a
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:DACIGVIOAFXPHW-UHFFFAOYSA-N
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Compound 51b
Molecular Weight:298.4623
Molecular Formula:C21H30O
InChIKey:RGWHHWWMFUXNAX-UHFFFAOYSA-N
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Compound 52
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 53b
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:Not Available
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Compound 53a
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:GENBEGZNCBFHSU-UHFFFAOYSA-N
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Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 55a
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YRKCREAYFQTBPV-UHFFFAOYSA-N
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Compound 55b
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YRKCREAYFQTBPV-UHFFFAOYSA-N
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Compound 56a
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:HJSLFCCWAKVHIW-UHFFFAOYSA-N
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Compound 56b
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:HJSLFCCWAKVHIW-UHFFFAOYSA-N
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Compound 57
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:DCZFGQYXRKMVFG-UHFFFAOYSA-N
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Compound 58a
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:CTDOPUVVTOMREJ-UHFFFAOYSA-N
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Compound 58b
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:JPBHXVRMWGWSMX-UHFFFAOYSA-N
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Compound 59
Molecular Weight:238.2812
Molecular Formula:C16H14O2
InChIKey:OSWWFLDIIGGSJV-UHFFFAOYSA-N
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Compound 60a
Molecular Weight:448.7644
Molecular Formula:C30H56O2
InChIKey:YCCUBQMBZRJIOM-UHFFFAOYSA-N
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Compound 60b
Molecular Weight:448.7644
Molecular Formula:C30H56O2
InChIKey:UPOMIGSAFIVGPH-UHFFFAOYSA-N
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Compound 63
Molecular Weight:69.1051
Molecular Formula:C4H7N
InChIKey:RSEBUVRVKCANEP-UHFFFAOYSA-N
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Compound 64a
Molecular Weight:207.3152
Molecular Formula:C12H21N3
InChIKey:POPXVWAQMYBXLI-UHFFFAOYSA-N
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Compound 64b
Molecular Weight:71.121
Molecular Formula:C4H9N
InChIKey:RWRDLPDLKQPQOW-UHFFFAOYSA-N
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Compound 65
Molecular Weight:83.1317
Molecular Formula:C5H9N
InChIKey:DWKUKQRKVCMOLP-UHFFFAOYSA-N
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Compound 66
Molecular Weight:149.2328
Molecular Formula:C10H15N
InChIKey:HWLZRTSLIFCZJR-UHFFFAOYSA-N
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Compound 67a
Molecular Weight:148.2447
Molecular Formula:C11H16
InChIKey:GBCSEMZQRBABQR-UHFFFAOYSA-N
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Compound 67b
Molecular Weight:151.2487
Molecular Formula:C10H17N
InChIKey:CRKHNIDATUGNFE-UHFFFAOYSA-N
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Compound 67c
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:LFWQUGCYGMCTQW-UHFFFAOYSA-N
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Compound 68a
Molecular Weight:105.1372
Molecular Formula:C7H7N
InChIKey:AFDMODCXODAXLC-UHFFFAOYSA-N
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Compound 68b
Molecular Weight:105.1372
Molecular Formula:C7H7N
InChIKey:NHNIVEADUHCPRP-UHFFFAOYSA-N
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Compound 69
Molecular Weight:181.2331
Molecular Formula:C13H11N
InChIKey:UVEWQKMPXAHFST-SDNWHVSQSA-N
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Compound 70a
Molecular Weight:168.2792
Molecular Formula:C10H20N2
InChIKey:HACCVLBYBQLWMC-MKICQXMISA-N
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Compound 70b
Molecular Weight:110.157
Molecular Formula:C6H10N2
InChIKey:APYDCJBHJXFOTJ-UHFFFAOYSA-N
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Compound 70c
Molecular Weight:236.3116
Molecular Formula:C16H16N2
InChIKey:QBAKBJNOARBSGP-HBKJEHTGSA-N
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Compound 71a
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:KAESVJOAVNADME-UHFFFAOYSA-N
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Compound 71b
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:JZIBVTUXIVIFGC-UHFFFAOYSA-N
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Compound 72a
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:SIKJAQJRHWYJAI-UHFFFAOYSA-N
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Compound 72b
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:RKJUIXBNRJVNHR-UHFFFAOYSA-N
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Compound 73a
Molecular Weight:68.0773
Molecular Formula:C3H4N2
InChIKey:RAXXELZNTBOGNW-UHFFFAOYSA-N
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Compound 73b
Molecular Weight:68.0773
Molecular Formula:C3H4N2
InChIKey:LGRQUXHYJBFGTM-UHFFFAOYSA-N
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Compound 74a
Molecular Weight:120.1121
Molecular Formula:C5H4N4
InChIKey:KDCGOANMDULRCW-UHFFFAOYSA-N
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Compound 74c
Molecular Weight:120.1121
Molecular Formula:C5H4N4
InChIKey:GPFABQVNFOPIDQ-UHFFFAOYSA-N
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Compound 74b
Molecular Weight:120.1121
Molecular Formula:C5H4N4
InChIKey:WZSGASVENYDXEQ-UHFFFAOYSA-N
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Compound 75a
Molecular Weight:237.2964
Molecular Formula:C16H15NO
InChIKey:CDCQPBZDRNRZSJ-UHFFFAOYSA-N
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Compound 75b
Molecular Weight:119.1638
Molecular Formula:C8H9N
InChIKey:LPAGFVYQRIESJQ-UHFFFAOYSA-N
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  1. 1 - 122