Weak hydrogen bonding .3. A benzyl group accepting equally strong hydrogen bonds from O-H and C-H donors: 5-ethynyl-5H-dibenzo[a,d]cyclohepten-5-ol

被引:57
作者
Steiner, T [1 ]
Starikov, EB [1 ]
Tamm, M [1 ]
机构
[1] FREE UNIV BERLIN,INST ANORGAN & ANALYT CHEM,D-14195 BERLIN,GERMANY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1996年 / 01期
关键词
D O I
10.1039/p29960000067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the crystal structure of the title compound, one of the benzyl groups accepts hydrogen bonds from a hydroxy and an ethynyl group, one to each face of the ring. For both hydrogen bonds, energies around -1.3 kcal mol(-1) have been calculated. The bond donated by the hydroxy group has unusual geometry and is directed almost linearly at a C atom with H...C = 2.36 Angstrom.
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收藏
页码:67 / 71
页数:5
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共 21 条
  • [1] THE DEVELOPMENT OF VERSION-3 AND VERSION-4 OF THE CAMBRIDGE STRUCTURAL DATABASE SYSTEM
    ALLEN, FH
    DAVIES, JE
    GALLOY, JJ
    JOHNSON, O
    KENNARD, O
    MACRAE, CF
    MITCHELL, EM
    MITCHELL, GF
    SMITH, JM
    WATSON, DG
    [J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1991, 31 (02): : 187 - 204
  • [2] X-RAY-DIFFRACTION EVIDENCE FOR AROMATIC PI HYDROGEN-BONDING TO WATER
    ATWOOD, JL
    HAMADA, F
    ROBINSON, KD
    ORR, GW
    VINCENT, RL
    [J]. NATURE, 1991, 349 (6311) : 683 - 684
  • [3] CRYSTAL-STRUCTURE OF TRIBUTYLAMMONIUM TETRAPHENYLBORATE MONOHYDRATE - EXAMPLE FOR H-PI INTERACTION
    AUBRY, A
    PROTAS, J
    MORENOGONZALEZ, E
    MARRAUD, M
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (AUG15): : 2572 - 2578
  • [4] THE C-H...O HYDROGEN-BOND IN CRYSTALS - WHAT IS IT
    DESIRAJU, GR
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) : 290 - 296
  • [5] CORRELATION BETWEEN CRYSTALLOGRAPHIC AND SPECTROSCOPIC PROPERTIES FOR C-H...O BONDS IN TERMINAL ACETYLENES
    DESIRAJU, GR
    MURTY, BN
    [J]. CHEMICAL PHYSICS LETTERS, 1987, 139 (3-4) : 360 - 361
  • [6] ENCODING AND DECODING HYDROGEN-BOND PATTERNS OF ORGANIC-COMPOUNDS
    ETTER, MC
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) : 120 - 126
  • [7] O-H ... PI(ARENE) INTERMOLECULAR HYDROGEN-BONDING IN THE STRUCTURE OF 1,1,2-TRIPHENYLETHANOL
    FERGUSON, G
    GALLAGHER, JF
    GLIDEWELL, C
    ZAKARIA, CM
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1994, 50 : 70 - 73
  • [8] Frisch MJ., 1992, GAUSSIAN 92 DFT REVI
  • [9] AROMATIC RINGS ACT AS HYDROGEN-BOND ACCEPTORS
    LEVITT, M
    PERUTZ, MF
    [J]. JOURNAL OF MOLECULAR BIOLOGY, 1988, 201 (04) : 751 - 754
  • [10] AMINO/AROMATIC INTERACTIONS IN PROTEINS - IS THE EVIDENCE STACKED AGAINST HYDROGEN-BONDING
    MITCHELL, JBO
    NANDI, CL
    MCDONALD, IK
    THORNTON, JM
    PRICE, SL
    [J]. JOURNAL OF MOLECULAR BIOLOGY, 1994, 239 (02) : 315 - 331