Resonance and conjugation—II Factors determining bond lengths and heats of formation

Dewar, Michael J. S.; Schmeising, H. N.

doi:10.1016/0040-4020(60)89012-6

Cited by 253 publications

(55 citation statements)

References 32 publications

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“…The C(1)-C(I') bond distance, 1.477 (8) A, is almost identical with that calculated theoretically, 1.479 A, for non-coplanar biphenyl (Dewar & Harget, 1970), and is not significantly different from the 1.489 A (being within 23) determined by X-ray analysis for 2,2'-dichlorobiphenyl (Romming et al, 1974). It should be pointed out that Dewar & Schmeising (1968) suggest 1.485 A as the length of a single bond between two sp 2-hybridized C atoms, which is within one e.s.d, of the value found in this work. The C-CI bond distances range from 1.720 (7) to 1.783 (7) A with a mean value of 1.730 A, which is within 20 of that found for decachlorobiphenyl, 1.718 A (Pedersen, 1975), and for hexachlorobenzene, 1.715 (2) A (Brown & Strydom, 1974).…”

Section: C1(4')-c(4')-c(5')supporting

confidence: 66%

2,2',4,4',6,6'-Hexachlorobiphenyl

Singh¹,

McKinney²

1979

Acta Crystallogr Sect B

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Section: C1(4')-c(4')-c(5')supporting

confidence: 66%

2,2',4,4',6,6'-Hexachlorobiphenyl

Singh¹,

McKinney²

1979

Acta Crystallogr Sect B

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“…The bond lengths N(2)-C(3) (1.300 A) and N(4)-C(9) (1.293 A) can be compared with those found for the five-membered rings of two azomethine dyes (Smith & Barrett, 1971). They seem to correspond to a N-C double bond (1.29 A: Pauling, 1960), whereas the bonds C(4)-C(5), C(8)-C(7), C(3)-C(4) and C(8)-C(9) are shorter than an sp2-sp 2 single bond (1.488 A" Dewar & Schmeising, 1960). The C-O distances are much longer than a C-O double bond and even longer than in 2-acetyl-3-indazolinone (Smith & Barrett, 1969) participates in an intermolecular hydrogen bond.…”

Section: Molecular Structurementioning

confidence: 99%

The structures of two rubazoic acid derivatives

Drück¹,

Littke²

1980

Acta Crystallogr Sect B

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“…The bond distances and bond angles in the title compound are similar to those found in other halogenated biphenyls. Thus, the C(1)-C(I') distance of 1.493 (7)A is within 2.0tr of that found for 2,2',4,4',6,6'-hexachlorobiphenyl [1.477 (8)A] (Singh & McKinney, 1979), and is only 1. ltr away from the theoretically calculated value, 1.485 A, between two sp2-hybridized C atoms (Dewar & Schmeising, 1968). The mean of the twelve C-C bond distances in the two benzene rings is 1.382 ,/k which is normal.…”

mentioning

confidence: 99%

Crystal and energy-refined structures of 2,2',4,4',5,5'-hexachlorobiphenyl

Singh¹,

Pedersen²,

McKinney³

1986

Acta Crystallogr C

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The bond distances and bond angles in the title compound are similar to those found in other halogenated biphenyls. The two benzene rings are planar; however, the two rings are not coplanar. Taking the trans-coplanar arrangement of C1(2) and C1(2') as 0 °, the dihedral angle between the rings is 58.3 °. The crystal structure is compared with the energyminimized molecular structures using the ab initio quantum-mechanical and molecular-mechanics methods, giving results in substantial agreement. The results are discussed for their possible use and importance in assessing the polychlorinated biphenyl ortho effect which appears to be important in determining receptor binding potency and toxicity of these compounds in biological systems.

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Resonance and conjugation—II Factors determining bond lengths and heats of formation

Cited by 253 publications

References 32 publications

2,2',4,4',6,6'-Hexachlorobiphenyl

2,2',4,4',6,6'-Hexachlorobiphenyl

The structures of two rubazoic acid derivatives

Crystal and energy-refined structures of 2,2',4,4',5,5'-hexachlorobiphenyl

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