Crystal engineering of primary cubanecarboxamides. Repetitive formation of an unexpected N-H···O hydrogen-bonded network

Kuduva, Srinivasan S. ; Blaser, Dieter ; Boese, Roland ; Desiraju, Gautam R. (2001) Crystal engineering of primary cubanecarboxamides. Repetitive formation of an unexpected N-H···O hydrogen-bonded network Journal of Organic Chemistry, 66 (5). pp. 1621-1626. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0013453

Related URL: http://dx.doi.org/10.1021/jo0013453

Abstract

The unusual N-H···O hydrogen bond pattern in a family of primary cubanecarboxamides is described. 4-Chloro-1-cubanecarboxamide, 1, and the corresponding bromo and iodo derivatives, 2 and 3, form the "shallow-glide"hydrogen-bonded motif instead of the usual 5.1 Å translated ribbon pattern, more characteristic of primary amides. This behavior is also seen, somewhat unexpectedly, for cubanecarboxamide, 4, but more or less unsurprisingly for 1,4-cubanedicarboxamide, 5. This repetitive occurrence of the same hydrogen bond pattern is of significance in crystal engineering wherein synthon robustness is measured in terms of such repetitivity. The cubyl group is directly responsible for the appearance of the shallow-glide motif in this family in preference to the 5.1 Å translation pattern for two reasons: (1) stericit is too large to fit in a 5.1 Å translated structure and (2) electronicits carbon acidity is sufficient to result in the appearance of C-H···O hydrogen bonds to the C=O group, disrupting any putative 5.1Å translated structure. Such a molecule → supermolecule relationship is of value in crystal engineering strategies.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:11502
Deposited On:16 Nov 2010 13:52
Last Modified:31 May 2011 04:21

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