Molecular Structure of Hexakis(dichloromethyl)benzene

Bart Kahr, Silvio E. Biali, Wolfgang Schaefer, Andrzej B. Buda, Kurt Mislow*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

The crystal and molecular structure of hexakis(dichloromethyl)benzene (2) has been determined. Crystals of 2 are triclinic, space group PI: a = 6.248 (1) Å, b = 9.749 (3) Å, c = 9.763 (2) Å, a = 116.32 (2)°, β = 94.97 (2)°, ϒ = 108.20 (2)°, Z = 1. The crystal structure and the dimensions of the unit cell closely resemble those previously found for hexaisopropylbenzene (1), and the molecules of 2, like those of 1, closely approximate C6h symmetry in the crystal. A crystallographic orientational disorder was resolved, and the population ratio of major and minor orientations, 1.827, was found to be similar in magnitude to the corresponding ratio for 1, 2.075. Empirical force-field calculations have revealed that in contrast to l,2-bis(dichloromethyl)- and pentakis(dichloromethyl)benzene, the conformations of lowest energy in 1,2-diisopropyl- and pentaisopropylbenzene are not gear-meshed and that 1 is unique among vicinally substituted polyisopropylbenzenes in having a ground-state conformation with homodirectional isopropyl groups.

Original languageAmerican English
Pages (from-to)3713-3717
Number of pages5
JournalJournal of Organic Chemistry
Volume52
Issue number17
DOIs
StatePublished - 1 Aug 1987
Externally publishedYes

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