12,15-Dichloro[3.0]orthometa- cyclophane: A Highly Strained Biphenylophane.

M.J. van Eis, F.J.J. de Kanter, W.H. de Wolf, F. Bickelhaupt

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

The title compound, 3, in which two methylene groups of the parent compound 4 have been replaced by an ortho-substituted benzene ring, has been synthesized. It exists exclusively in the endo-conformation, in contrast to 4 for which the exo-conformation is preferred. High-level density functional calculations are presented for both compounds. They show that the endo- conformation of 3 is favored over the exo-conformation by 3.3 kcal mol
Original languageEnglish
Pages (from-to)3371-3375
JournalJournal of the American Chemical Society
Volume120
Issue number14
DOIs
Publication statusPublished - 1998

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Conformations
Benzene
Density functional theory

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van Eis, M. J., de Kanter, F. J. J., de Wolf, W. H., & Bickelhaupt, F. (1998). 12,15-Dichloro[3.0]orthometa- cyclophane: A Highly Strained Biphenylophane. Journal of the American Chemical Society, 120(14), 3371-3375. https://doi.org/10.1021/ja973876n
van Eis, M.J. ; de Kanter, F.J.J. ; de Wolf, W.H. ; Bickelhaupt, F. / 12,15-Dichloro[3.0]orthometa- cyclophane: A Highly Strained Biphenylophane. In: Journal of the American Chemical Society. 1998 ; Vol. 120, No. 14. pp. 3371-3375.
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abstract = "The title compound, 3, in which two methylene groups of the parent compound 4 have been replaced by an ortho-substituted benzene ring, has been synthesized. It exists exclusively in the endo-conformation, in contrast to 4 for which the exo-conformation is preferred. High-level density functional calculations are presented for both compounds. They show that the endo- conformation of 3 is favored over the exo-conformation by 3.3 kcal mol",
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van Eis, MJ, de Kanter, FJJ, de Wolf, WH & Bickelhaupt, F 1998, '12,15-Dichloro[3.0]orthometa- cyclophane: A Highly Strained Biphenylophane.' Journal of the American Chemical Society, vol. 120, no. 14, pp. 3371-3375. https://doi.org/10.1021/ja973876n

12,15-Dichloro[3.0]orthometa- cyclophane: A Highly Strained Biphenylophane. / van Eis, M.J.; de Kanter, F.J.J.; de Wolf, W.H.; Bickelhaupt, F.

In: Journal of the American Chemical Society, Vol. 120, No. 14, 1998, p. 3371-3375.

Research output: Contribution to JournalArticleAcademicpeer-review

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AU - van Eis, M.J.

AU - de Kanter, F.J.J.

AU - de Wolf, W.H.

AU - Bickelhaupt, F.

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AB - The title compound, 3, in which two methylene groups of the parent compound 4 have been replaced by an ortho-substituted benzene ring, has been synthesized. It exists exclusively in the endo-conformation, in contrast to 4 for which the exo-conformation is preferred. High-level density functional calculations are presented for both compounds. They show that the endo- conformation of 3 is favored over the exo-conformation by 3.3 kcal mol

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JF - Journal of the American Chemical Society

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