Systematic analysis of the probabilities of formation of bimolecular hydrogen-bonded ring motifs in organic crystal structures

被引:366
作者
Allen, FH
Motherwell, WDS
Raithby, PR
Shields, GP
Taylor, R
机构
[1] Cambridge Crystallog Data Ctr, Cambridge CB2 1EZ, England
[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
D O I
10.1039/a807212d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A methodology has been developed for characterising hydrogen-bonded ring motifs formed between two organic molecules without any prior knowledge of the topology or chemical constitution of the motifs. The method has been implemented by modifying the current Cambridge Structural Database (CSD) System programs. All intermolecular ring motifs comprising less than or equal to 20 atoms formed with N-H ... N, N-H ... O, O-H ... N and O-H ... O hydrogen bonds in organic structures in the CSD have been classified. The 75 bimolecular motifs occurring in > 12 structures in the CSD are described in terms of their graph sets and chemical functionalities. Motifs are ranked according to their frequency of occurrence and according to their probabilities of formation, i.e. their frequency relative to the number of possible motifs which could have formed. These probabilities provide insights into the relative robustness of known and potential supramolecular synthons.
引用
收藏
页码:25 / 34
页数:10
相关论文
共 47 条
[1]   THE HYDROGEN-BOND AND CRYSTAL ENGINEERING [J].
AAKEROY, CB ;
SEDDON, KR .
CHEMICAL SOCIETY REVIEWS, 1993, 22 (06) :397-407
[2]   FORMATION OF MOLECULAR STRANDS BY HYDROGEN-BONDS AT THE GAS WATER INTERFACE - MOLECULAR RECOGNITION AND QUANTITATIVE HYDROLYSIS OF BARBITURIC-ACID LIPIDS [J].
AHUJA, R ;
CARUSO, PL ;
MOBIUS, D ;
PAULUS, W ;
RINGSDORF, H ;
WILDBURG, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1033-1036
[3]  
Allen F.H., 1993, CHEM AUTOMAT NEWS, V8, P31
[4]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[5]   Probabilities of formation of bimolecular cyclic hydrogen-bonded motifs in organic crystal structures: a systematic database analysis [J].
Allen, FH ;
Raithby, PR ;
Shields, GP ;
Taylor, R .
CHEMICAL COMMUNICATIONS, 1998, (09) :1043-1044
[6]  
ALLEN FH, UNPUB ACTA CRYSTAL B
[7]  
[Anonymous], 1965, COMPUTING METHODS CR
[8]  
BAILINGER WF, 1964, TETRAHEDRON, V20, P1635
[9]   COMPLEXATION OF CARBONYL-COMPOUNDS WITH AN ORGANIC SALT DOMINATED BY ACID-BASE INTERACTIONS IN DICHLOROMETHANE [J].
BELL, DA ;
ANSLYN, EV .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :512-514
[10]   POLYMORPHISM OF L-GLUTAMIC ACID - DECODING THE ALPHA-BETA PHASE RELATIONSHIP VIA GRAPH-SET ANALYSIS [J].
BERNSTEIN, J .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1991, 47 :1004-1010