Standard Article

Thermochemistry of Dienes and Polyenes

Dienes and Polyenes (1997)

  1. Joel F. Liebman

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0099

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Liebman, J. F. 2009. Thermochemistry of Dienes and Polyenes . Patai's Chemistry of Functional Groups. .

Author Information

  1. University of Maryland, Department of Chemistry and Biochemistry, Baltimore County Campus, Baltimore, Maryland, USA

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction: Scope and Definitions
  • 2
    Nonconjugated Dienes and Polyenes
  • 3
    Cumulated Or Allenic Dienes and Polyenes (Cumulenes)
  • 4
    Conjugated Acyclic Dienes
  • 5
    Cyclic Dienes
  • 6
    Conjugated Polyenes
  • 7
    Conjugated Species With Exo-Methylene Groups: Fulvenes, Isotoluenes, Xylylenes and Related Species
  • 8
    Annulenes: Aromaticity and Antiaromaticity
  • 9
    Acknowledgments

Keywords:

  • diene and polyene thermochemistry;
  • nonconjugated dienes and polyenes;
  • cumulated or allenic dienes and polyenes (cumulenes);
  • conjugated acyclic dienes;
  • cyclic dienes;
  • doubly exo cyclic dienes;
  • acyclic conjugated diene thermochemistry;
  • annulenes - aromaticity and antiaromaticity

Featured Compounds

VIEW

  1. 1 - 150
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:Not Available
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Compound 2
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:LVMTVPFRTKXRPH-UHFFFAOYSA-N
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Compound 4
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:Not Available
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Compound 5
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:Not Available
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Compound 6
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound 7
Molecular Weight:128.1705
Molecular Formula:C10H8
InChIKey:UFWIBTONFRDIAS-UHFFFAOYSA-N
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Compound 8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48
Molecular Weight:66.1011
Molecular Formula:C5H6
InChIKey:ZSWFCLXCOIISFI-UHFFFAOYSA-N
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Compound 90
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:OORRQYZWSVJKSO-UHFFFAOYSA-N
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 49
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:Not Available
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Compound 50
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:UVJHQYIOXKWHFD-UHFFFAOYSA-N
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Compound 13
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:PYGSKMBEVAICCR-UHFFFAOYSA-N
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Compound 14
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:PRBHEGAFLDMLAL-XQRVVYSFSA-N
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Compound 15
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:Not Available
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Compound 16
Molecular Weight:Not Available
Molecular Formula:(CH2)nC2H2
InChIKey:OOXWYYGXTJLWHA-UHFFFAOYSA-N
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Compound 53
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:URYYVOIYTNXXBN-UPHRSURJSA-N
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Compound 139
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N
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Compound 17
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:UCAJIFZNHMIWOD-ARJAWSKDSA-N
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Compound 18
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:UCAJIFZNHMIWOD-ARJAWSKDSA-N
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Compound 19
Molecular Weight:76.096
Molecular Formula:C6H4
InChIKey:Not Available
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Compound 20
Molecular Weight:76.096
Molecular Formula:C6H4
InChIKey:KLYCPFXDDDMZNQ-UHFFFAOYSA-N
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Compound 21
Molecular Weight:74.0801
Molecular Formula:C6H2
InChIKey:HSKFQZXXRPRBEJ-UHFFFAOYSA-N
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Compound 22
Molecular Weight:76.096
Molecular Formula:C6H4
InChIKey:AIESRBVWAFETPR-UHFFFAOYSA-N
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Compound 23
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:YTNGLTTXVJWZKF-UHFFFAOYSA-N
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Compound 24
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:LAUMUDIRLSPOKG-UHFFFAOYSA-N
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Compound 25
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:ADAQQPDXZURMQF-UHFFFAOYSA-N
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Compound 27
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:ADAQQPDXZURMQF-UHFFFAOYSA-N
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Compound 28
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:ADAQQPDXZURMQF-UHFFFAOYSA-N
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Compound 29
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:Not Available
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Compound 26
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:VYXHVRARDIDEHS-QGTKBVGQSA-N
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Compound 30
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:VYXHVRARDIDEHS-CDTWYVJESA-N
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Compound 31
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:VYXHVRARDIDEHS-GQUYQXFZSA-N
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Compound 33
Molecular Weight:166.3031
Molecular Formula:C12H22
InChIKey:XOJJYBDDNRTSIT-UHFFFAOYSA-N
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Compound 34
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:PBGBMQLUDCDJQJ-KQQUZDAGSA-N
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Compound 35
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:PBGBMQLUDCDJQJ-CGXWXWIYSA-N
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Compound 36
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:PBGBMQLUDCDJQJ-SFECMWDFSA-N
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Compound 82
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:RRHGJUQNOFWUDK-UHFFFAOYSA-N
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Compound 144
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:APPOKADJQUIAHP-GLIMQPGKSA-N
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Compound 145
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:APPOKADJQUIAHP-CIIODKQPSA-N
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Compound 146
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:APPOKADJQUIAHP-GGWOSOGESA-N
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Compound 37
Molecular Weight:206.2824
Molecular Formula:C16H14
InChIKey:JFLKFZNIIQFQBS-PVRNWPCDSA-N
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Compound 38
Molecular Weight:206.2824
Molecular Formula:C16H14
InChIKey:JFLKFZNIIQFQBS-FNCQTZNRSA-N
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Compound 39
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-QXMHVHEDSA-N
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Compound 40
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-VAWYXSNFSA-N
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Compound 41
Molecular Weight:358.4743
Molecular Formula:C28H22
InChIKey:DAABVBOFAIYKNX-GPAWKIAZSA-N
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Compound 42
Molecular Weight:358.4743
Molecular Formula:C28H22
InChIKey:Not Available
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Compound 47
Molecular Weight:66.1011
Molecular Formula:C5H6
InChIKey:VRNCRGHDRGGBLW-UHFFFAOYSA-N
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Compound 51
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:GWYPDXLJACEENP-UHFFFAOYSA-N
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Compound 52
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:HQGYGGZHZWXFSI-UHFFFAOYSA-N
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Compound 54
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:URYYVOIYTNXXBN-OWOJBTEDSA-N
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Compound 55a
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:DNZZPKYSGRTNGK-PQZOIKATSA-N
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Compound 55b
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:RRKODOZNUZCUBN-HSFFGMMNSA-N
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Compound 56
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:DNZZPKYSGRTNGK-PQZOIKATSA-N
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Compound 57
Molecular Weight:66.1011
Molecular Formula:C5H6
InChIKey:ZNKWTJLYBOAVHI-UHFFFAOYSA-N
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Compound 58
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:QOFLWDYWJZBWHM-UHFFFAOYSA-N
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Compound 59
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:QIRVGKYPAOQVNP-UHFFFAOYSA-N
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Compound 60
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:DTSPMBOMCCTXSG-UHFFFAOYSA-N
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Compound 61
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:BDJAEZRIGNCQBZ-UHFFFAOYSA-N
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Compound 62
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:WKHRDGKOKYBNDZ-UHFFFAOYSA-N
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Compound 63
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:XBJHZEUYCYYCLK-UHFFFAOYSA-N
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Compound 64
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:DPUPESLAFGZQOY-UHFFFAOYSA-N
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Compound 66
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:JPBHXVRMWGWSMX-UHFFFAOYSA-N
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Compound 65
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:CTDOPUVVTOMREJ-UHFFFAOYSA-N
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Compound 67
Molecular Weight:Not Available
Molecular Formula:(CH2)nC4H4
InChIKey:AQSOFHKMDGNCDW-UHFFFAOYSA-N
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Compound 68
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H6
InChIKey:SJYNFBVQFBRSIB-UHFFFAOYSA-N
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Compound 69
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H8
InChIKey:JFNLZVQOOSMTJK-UHFFFAOYSA-N
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Compound 70
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H10
InChIKey:UMRZSTCPUPJPOJ-UHFFFAOYSA-N
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Compound 71
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:RHCCUQVVABYRDN-UHFFFAOYSA-N
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Compound 72
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:HKRMLKXSBBQRIM-UHFFFAOYSA-N
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Compound 73
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:WFYJSBGFDIPAEJ-UHFFFAOYSA-N
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Compound 74
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:KWMNZJNIAZZNSJ-UHFFFAOYSA-N
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Compound 75
Molecular Weight:536.8726
Molecular Formula:C40H56
InChIKey:OENHQHLEOONYIE-JLTXGRSLSA-N
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Compound 76
Molecular Weight:284.4357
Molecular Formula:C20H28O
InChIKey:Not Available
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Compound 77
Molecular Weight:Not Available
Molecular Formula:(C2H2)nC4H6
InChIKey:AFVDZBIIBXWASR-AATRIKPKSA-N
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Compound 78
Molecular Weight:382.6218
Molecular Formula:C27H42O
InChIKey:RQOCXCFLRBRBCS-SOFGYWHQSA-N
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Compound 79
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:AFVDZBIIBXWASR-WAYWQWQTSA-N
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Compound 80
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:AFVDZBIIBXWASR-AATRIKPKSA-N
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Compound 81
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:ZVFFWOKVVPSTAL-AATRIKPKSA-N
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Compound 83
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:UBFBTMRIJJRZOA-WAYWQWQTSA-N
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Compound 84
Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:BOBLSBAZCVBABY-WPWUJOAOSA-N
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Compound 85
Molecular Weight:Not Available
Molecular Formula:(C2H2)nC12H10
InChIKey:PJANXHGTPQOBST-VAWYXSNFSA-N
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Compound 86
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:CHVJITGCYZJHLR-UHFFFAOYSA-N
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Compound 87
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:Not Available
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Compound 88
Molecular Weight:146.2289
Molecular Formula:C11H14
InChIKey:POQPGBIFWKXZAJ-UHFFFAOYSA-N
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Compound 89
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:FKGSJFRETKUFML-UHFFFAOYSA-N
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Compound 91
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:CXWXQJXEFPUFDZ-UHFFFAOYSA-N
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Compound 92
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:FUPIVZHYVSCYLX-UHFFFAOYSA-N
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Compound 93
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:WOLNCZXFBFSYFC-UHFFFAOYSA-N
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Compound 94
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:NBQVIMNMHQYULH-UHFFFAOYSA-N
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Compound 95
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:PQNFLJBBNBOBRQ-UHFFFAOYSA-N
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Compound 96
Molecular Weight:168.1832
Molecular Formula:C10H10F2
InChIKey:WPRGKVFFUILSES-UHFFFAOYSA-N
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Compound 97
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:CDABYMXFMPXNAL-UHFFFAOYSA-N
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Compound 98
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:HAQWKXYXEKTGMS-UHFFFAOYSA-N
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Compound 99
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:PVDVWMOTLDWVRK-FLXUIKBISA-N
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Compound 100
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:IMTIYIKRBGNQTQ-VAWYXSNFSA-N
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Compound 101
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:IMTIYIKRBGNQTQ-QXMHVHEDSA-N
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Compound 102
Molecular Weight:160.2554
Molecular Formula:C12H16
InChIKey:IGARGHRYKHJQSM-UHFFFAOYSA-N
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Compound 121
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:WHCRVRGGFVUMOK-UHFFFAOYSA-N
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Compound 103
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:PGTKVMVZBBZCKQ-UHFFFAOYSA-N
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Compound 105
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:GGKMDDDYCSVHMU-UHFFFAOYSA-N
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Compound 106
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:OSBSXTGABLIDRX-UHFFFAOYSA-N
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Compound 107
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:LVRLCNCYLXWRNI-UHFFFAOYSA-N
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Compound 108
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:HVUHAGAKMQKWKQ-UHFFFAOYSA-N
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Compound 109
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:DPJQAOVDKNHBFY-UHFFFAOYSA-N
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Compound 110
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:NUOVRNYCJGXOAA-UHFFFAOYSA-N
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Compound 111
Molecular Weight:192.2558
Molecular Formula:C15H12
InChIKey:JKJIYCKJURHVEF-UHFFFAOYSA-N
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Compound 112
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:QPUYECUOLPXSFR-UHFFFAOYSA-N
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Compound 113
Molecular Weight:192.2558
Molecular Formula:C15H12
InChIKey:CPGPAVAKSZHMBP-UHFFFAOYSA-N
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Compound 114
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:XURVRZSODRHRNK-UHFFFAOYSA-N
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Compound 115
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:NRNFFDZCBYOZJY-UHFFFAOYSA-N
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Compound 116
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:WOAHJDHKFWSLKE-UHFFFAOYSA-N
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Compound 117
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound 118
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:IAJQBWKVTDKBHW-UHFFFAOYSA-N
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Compound 119
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:IVSZLXZYQVIEFR-UHFFFAOYSA-N
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Compound 120
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 122
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:VXBVLYQDVVHAHZ-UHFFFAOYSA-N
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Compound 123
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:WMLZREYCISVLDD-VOTSOKGWSA-N
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Compound 124
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:DMCINEDFOKMBFI-UHFFFAOYSA-N
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Compound 125
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:VXQUABLSXKFKLO-KQQUZDAGSA-N
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Compound 126
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:ZMYIIHDQURVDRB-UHFFFAOYSA-N
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Compound 127
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 129
Molecular Weight:230.3038
Molecular Formula:C18H14
InChIKey:BULLHRADHZGONG-UHFFFAOYSA-N
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Compound 131
Molecular Weight:134.2182
Molecular Formula:C10H14
InChIKey:RYLMKTLFCIGRQD-UHFFFAOYSA-N
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Compound 132
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 134
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:GYNNXHKOJHMOHS-UHFFFAOYSA-N
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Compound 135
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:QVWDCTQRORVHHT-UHFFFAOYSA-N
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Compound 136
Molecular Weight:486.6448
Molecular Formula:C38H30
InChIKey:FWSYACUVHKGULL-UHFFFAOYSA-N
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Compound 137
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:CXHZYOISZDAYCU-ALCCZGGFSA-N
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Compound 138
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:Not Available
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Compound 140
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:UMIVXZPTRXBADB-UHFFFAOYSA-N
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Compound 141
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:RPZUBXWEQBPUJR-UHFFFAOYSA-N
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Compound 142
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:CTQNGGLPUBDAKN-UHFFFAOYSA-N
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Compound 143
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:URLKBWYHVLBVBO-UHFFFAOYSA-N
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Compound 147
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:Not Available
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Compound 148
Molecular Weight:208.2982
Molecular Formula:C16H16
InChIKey:RDEIDWDSOWVJQA-LIPBRFHFSA-N
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Compound 149
Molecular Weight:234.3355
Molecular Formula:C18H18
InChIKey:STQWAGYDANTDNA-DWSNDWDZSA-N
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Compound 150
Molecular Weight:156.2237
Molecular Formula:C12H12
InChIKey:DPOGCTHIXSJOQN-VHOZIDCHSA-N
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Compound 151
Molecular Weight:236.3514
Molecular Formula:C18H20
InChIKey:WKVJZDZQEMUPHN-LHWURSEJSA-N
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Compound 152
Molecular Weight:102.1332
Molecular Formula:C8H6
InChIKey:GUVXZFRDPCKWEM-UHFFFAOYSA-N
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Compound 153
Molecular Weight:128.1705
Molecular Formula:C10H8
InChIKey:CUFNKYGDVFVPHO-UHFFFAOYSA-N
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Compound 154
Molecular Weight:128.1705
Molecular Formula:C10H8
InChIKey:FPEVLUDJYTXDPD-CKSLBRPTSA-N
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Compound 155
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:OVPVGJFDFSJUIG-VFLSUHNHSA-N
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Compound 156
Molecular Weight:270.4522
Molecular Formula:C20H30
InChIKey:LSMDTOOJZQSBES-UHFFFAOYSA-N
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Compound 157
Molecular Weight:182.261
Molecular Formula:C14H14
InChIKey:RYQWRHUSMUEYST-PDVBCDSSSA-N
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Compound 158
Molecular Weight:184.2768
Molecular Formula:C14H16
InChIKey:BXXAZCMIYPYZKT-IPPUEFGVSA-N
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