ISSN:
1573-1111
Keywords:
Amide hosts
;
benzene
;
hydrogen bonding
;
edge-face and face-face aromatic interactions
;
Ritter reaction
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract 5H-Dibenzo[a, d]cyclohepten-5-ol1 can undergo Ritter reaction with acetonitrile and sulfuric acid to afford either the acetamide derivative2 or the multicyclic amide3 depending on the conditions used. The X-ray structure of the inclusion compound of3 with benzene is reported here and analysed in structural terms. This material [(C19H18N2O)−(C6H6),Cc,a=10.694(5),b=22.843(5),c=9.901(4) Å,β=124.02(2)°,Z=4,R=0.054] has molecules of3 linked by −N−H⋯O=C intermolecular hydrogen bonds to form parallel chains alongc. Additional inter-host stabilisation is achieved by face-face interactions involving one of the two benzo rings of3. A hydrogen atom of the other host benzo group participates in an edge-face interaction with the benzene guest molecule to produce the inclusion compound. Benzene⋯benzene inter-guest interactions provide a further, but minor, contribution to the net stability of the structure.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00708880
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