Critical evaluation of C-H•••X hydrogen bonding in the crystalline state

被引:191
作者
van den Berg, JA [1 ]
Seddon, KR [1 ]
机构
[1] Queens Univ Belfast, QUILL Ctr, Belfast BT9 5AG, Antrim, North Ireland
关键词
D O I
10.1021/cg034083h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Contacts of the type C-H...X where X = F, Cl, Br, I, O, S, or N were analyzed statistically using structures available in the Cambridge Structural Database. For this analysis, the cone correction method was extended to an isotropic density correction. This method corrects for both angular and distance effects by normalizing isotropic contact densities from the experimental distributions. It was possible to show the widespread occurrence of C-H...X interactions in the crystalline state using this method. Distances of highest incidence, at which the largest number of contacts were sampled after normalization of isotropic distribution, were determined for each interaction type. These distances were compared to the classically accepted van der Waals cutoff radii, often used to distinguish between hydrogen-bonded interactions and van der Waals contacts. Generally, distances of highest incidence did not occur at the sum of van der Waals cutoff radii but occurred either below or above that distance depending on the specific interaction analyzed. This methodology, while of course not yielding quantitative data on hydrogen bond strength, allowed for a qualitative ordering of the interactions studied, in terms of expected interaction strengths.
引用
收藏
页码:643 / 661
页数:19
相关论文
共 47 条
[1]   The C-H•••Cl hydrogen bond:: Does it exist? [J].
Aakeröy, CB ;
Evans, TA ;
Seddon, KR ;
Pálinkó, I .
NEW JOURNAL OF CHEMISTRY, 1999, 23 (02) :145-152
[2]   THE HYDROGEN-BOND AND CRYSTAL ENGINEERING [J].
AAKEROY, CB ;
SEDDON, KR .
CHEMICAL SOCIETY REVIEWS, 1993, 22 (06) :397-407
[3]   Applications of the Cambridge Structural Database in organic chemistry and crystal chemistry [J].
Allen, FH ;
Motherwell, WDS .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2002, 58 :407-422
[4]   The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[5]  
[Anonymous], 1992, RECOMBINANT DNA
[6]   Metal-bound chlorine often accepts hydrogen bonds [J].
Aullón, G ;
Bellamy, D ;
Brammer, L ;
Bruton, EA ;
Orpen, AG .
CHEMICAL COMMUNICATIONS, 1998, (06) :653-654
[7]   Divalent complexes of 3-hydroxy-4-methyl-2(3H)-thiazolethione with Co-Zn:: synthesis, X-ray crystal structures and the structure-directing influence of C-H•••S interactions [J].
Bond, AD ;
Jones, W .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, Royal Society of Chemistry (20) :3045-3051
[8]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+
[9]   Fluoride ligands exhibit marked departures from the hydrogen bond acceptor behavior of their heavier halogen congeners [J].
Brammer, L ;
Bruton, EA ;
Sherwood, P .
NEW JOURNAL OF CHEMISTRY, 1999, 23 (10) :965-968
[10]   New software for searching the Cambridge Structural Database and visualizing crystal structures [J].
Bruno, IJ ;
Cole, JC ;
Edgington, PR ;
Kessler, M ;
Macrae, CF ;
McCabe, P ;
Pearson, J ;
Taylor, R .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2002, 58 :389-397