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Volumn 3, Issue 4, 2003, Pages 581-585

Crystal engineering: Identification of a unique supramolecular synthon based on C=O⋯X interaction in halogen-substituted aromatic carboxaldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; BROMINE DERIVATIVE; HALOGEN;

EID: 0037828148     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg034001p     Document Type: Article
Times cited : (57)

References (40)
  • 5
    • 0141545388 scopus 로고
    • and references therein
    • Desiraju, G. R. Chem. Commun. 1907, 1475 and references therein.
    • (1907) Chem. Commun. , pp. 1475
    • Desiraju, G.R.1
  • 7
    • 0003653494 scopus 로고    scopus 로고
    • Oxford University Press: Oxford, U. K.
    • The functional group approach for crystal structure design and prediction is not entirely viable. Recent investigations have shown that the simultaneous operation of weaker interactions and strong and directional O-H⋯O hydrogen bonds leads to departure from the expectations based on molecular association via strong interactions alone, see Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, U. K., 1999.
    • (1999) The Weak Hydrogen Bond in Structural Chemistry and Biology
    • Desiraju, G.R.1    Steiner, T.2
  • 15
    • 0141545386 scopus 로고    scopus 로고
    • note
    • We have preferred to term "C-H⋯X" as an interaction to a "hydrogen bond". The question of whether the C-H⋯X interaction involving formyl hydrogens can be called a hydrogen bond will be addressed elsewhere.
  • 16
    • 0141545387 scopus 로고    scopus 로고
    • note
    • The details of the crystal structure determination for 3 and 7 have been already reported, see ref 12.
  • 17
    • 0002464446 scopus 로고    scopus 로고
    • MacNicol, D. D., Toda, F., Bishop, R., Eds.; Pergamon Press: Oxford
    • Herbstein, F. H. In Comprehensive Supramolecular Chemistry; MacNicol, D. D., Toda, F., Bishop, R., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, p 61.
    • (1996) Comprehensive Supramolecular Chemistry , vol.6 , pp. 61
    • Herbstein, F.H.1
  • 28
    • 0037244412 scopus 로고    scopus 로고
    • The C=O⋯Br distance of 3.44 Å in the case of triclinic modification, i.e., 2T, is larger than the sum of van der Waals radii. This is presumably due to crystal packing forces. The directionality as reflected from the C-X⋯O=C angle leaves no doubt as to the anisotropic interaction. Indeed, the assessment of the strength of an interaction based on distance criterion alone can be misleading. It has been shown that the position of minimum in the intermolecular potential is ca. 0.4 Å larger than the van der Waals distance, see Dance, I. New J. Chem. 2003, 27, 22.
    • (2003) New J. Chem. , vol.27 , pp. 22
    • Dance, I.1
  • 30
    • 0141545385 scopus 로고    scopus 로고
    • note
    • A similar isostructurality in the crystal structures of 2,5-dichloro- and 2,5-dibromo-1,4-benzoquinones has been attributed to the effectiveness of C=O⋯X interactions, see ref 27. For discussion on the crystal packing of a variety of halogen-substituted benzoquinones, see ref 22.
  • 31
    • 0141545384 scopus 로고    scopus 로고
    • note
    • C-Br⋯O = 168.7°). The absence of the dimeric motif 1 in the remaining compounds is found to be due to the presence of other functional groups such as Br, OH, COOH, etc., which are capable of stabilizing the crystal lattice through interactions of their own. The alternative and equally or better-stabilizing interactions appear to obviate the adoption of dimeric motif 1 in all these cases.
  • 33
    • 0030696761 scopus 로고    scopus 로고
    • and references therein
    • Desiraju, G. R. Science 1997, 278, 404 and references therein.
    • (1997) Science , vol.278 , pp. 404
    • Desiraju, G.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.