Formyl C-H···O hydrogen bonding in crystalline bis-formamides?

Journal of the American Chemical Society

Volumn 118, Issue 39, 1996, Pages 9432-9433

  Chaney, Jason D ^a   Goss, Christopher R ^b   Folting, Kirsten ^a   Santarsiero, Bernard D ^c   Hollingsworth, Mark D ^a,b  

^a INDIANA UNIVERSITY   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORMAMIDE;

ARTICLE; CRYSTALLOGRAPHY; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY;

EID: 0029952122     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960637b     Document Type: Article

References (27)

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7. Formyl C-H bonds were normalized to the standard neutron length (1.083 Å) before these searches, which excluded substructures containing metals bound to the formyl oxygen. H⋯O contacts as short as 2.20 Å were observed.
8. Neuheuser, T.; Hess, B. A.; Reutel, C.; Weber, E. J. Phys. Chem. 1994, 98, 6459-6467.
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12. 6) and that it is the only suitable recrystallization solvent we have found for these bis-formamides.
13. Ohki, M.; Takenaka, A.; Shimanouchi, H.; Sasada, Y. Bull. Chem. Soc. Jpn. 1975, 48, 848-852.
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15. WF = 0.086, GOF = 2.60.
16. WF = 0.055, GOF = 3.25.
17. WF = 0.072, GOF = 3.195.
18. The structure of EDDF also contains short formyl C-H⋯O contacts and a twisted chain conformation that allows their occurrence. This structure will be reported elsewhere.
19. See: Hollingsworth, M. D.; Brown, M. E.; Santarsiero, B. D.; Huffman, J. C.; Goss, C. R. Chem. Mater. 1994, 6, 1227-1244.
20. (a) King, S. T. J. Phys. Chem. 1971, 75, 405-410.
21. (b) Smith, C. H.; Thompson, R. H. J. Mol. Spectrosc. 1972, 42, 227-238.
22. After an exhaustive search for polymorphism, we conclude that the structures shown here represent the bulk properties of these samples.
23. -1.
24. -1. See: Nielsen, O. F.; Christensen, D. H.; Rasmussen, O. H. J. Mol. Struct. 1991, 242, 273-282.)
25. Vinogradov, S. N.; Linnell, R. H. Hydrogen Bonding; van Nostrand Reinhold Co.: New York, 1971; pp 47-64.
26. Wiberg, K. B.; Waldron, R. F.; Schulte, G.; Sanuders, M. J. Am. Chem. Soc. 1991, 113, 971-977.
27. 1) and 0.836 (1) when C-H distances were constrained to be 1.083 Å.