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Title: Stereoelectronic control on the energy barrier to rotation about N-C (phenyl) bond
Authors: Srivastav, Kamal K
Srivastava, Vandana
Verma, Shiva M
Bharadwaja, P K
Issue Date: Jun-1999
Publisher: NISCAIR-CSIR, India
Abstract: Conformational analysis about the N-C (aryl) bond in N-arylsuccinimidyl system incorporating different dissymmetric cages indicates that besides the steric and electronic interaction of ortho-substituents, the dissymmetric cage also plays an important role in controlling the torsional barrier. In the case of anthracenemaleic anhydride adduct system, two stable rotamers about the N-C (phenyl) bond with 2'-methyl and 6'-ethyl substituents are isolated, whereas with such substituents rotamers are not isolable with cyclopentadiene-maleic anhydride and hexachlorocyclopentadiene-maleic anhydride (HCCPD-MA) adduct cages. X-ray crystallography of the HCCPD-MA system with two methyls at 2'-and 6'-positions in the phenyl ring (as in 5b) demonstrats an orthogonal geometry of the aryl ring with respect to the succinimidyl plane. The endo-configuration of the adduct 5 has also been established.
Page(s): 672-678
Appears in Collections:IJC-B Vol.38B(06) [June 1999]

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