Structures and Photoreactivities of 2,4,6-Triisopropylbenzophenones

Shigeru Fukushima, Yoshikatsu Ito, Hiroyuki Hosomi, Shigeru Ohba

研究成果: Article査読

16 被引用数 (Scopus)

抄録

Crystal structures of 2,4,6-triisopropylbenzophenone (I) and its ten derivatives have been determined: (II) 2,4,6-triisopropyl-3′-methoxybenzophenone, (III) 3′-chloroformyl-2,4,6-triisopropylbenzophenone, (IV) methyl 3-(2,4,6-triisopropylbenzoyl)benzoate, (V) 2,4,6-triisopropyl-4′-methylbenzophenone, (VI) 4′-tert-butyl-2,4,6-triisopropylbenzophenone, (VII) 2,4,6-triisopropyl-4′-methoxybenzophenone, (VIII) 4-(2,4,6-triisopropylbenzoyl)benzoic acid, (IX) 4′-chloroformyl-2,4,6-triisopropylbenzophenone, (X) methyl 4-(2,4,6-triisopropylbenzoyl)benzoate and (XI) ethyl 4-(2,4,6-triisopropylbenzoyl)benzoate. The conformations of these molecules are essentially the same. The central carbonyl moiety is approximately coplanar with the 3′- or 4′-substituted phenyl group and perpendicular to the triisopropylphenyl ring. The photostability of (IX) and (X) in the solid state is attributed to the narrow reaction cavity of the triisopropylphenylcarbonyl moiety, i.e. the intramolecular movements of isopropyl groups in the triisopropylphenyl plane toward the carbonyl C atom are suppressed by intermolecular close contacts. One of the barriers for the photocyclization of (IX) and (X) is caused by a dimeric structure in crystals through the π-π interaction, which is the result of having a polar methoxycarbonyl or chloroformyl group at position 4′ of the phenyl ring.

本文言語English
ページ(範囲)895-906
ページ数12
ジャーナルActa Crystallographica Section B: Structural Science
54
6
DOI
出版ステータスPublished - 1998 12 1

ASJC Scopus subject areas

  • 生化学、遺伝学、分子生物学(全般)

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