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Volumn 103, Issue 46, 1999, Pages 9164-9166

Hydrogen bond strength and acidity. Structural and energetic correlations for acetylides and alcohols

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EID: 0042635310     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (2)

References (35)
  • 4
    • 0008028137 scopus 로고
    • For recent gas-phase work see: Meot-Ner, M. J. Am. Chem. Soc. 1984, 106, 1257-1264;
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 1257-1264
    • Meot-Ner, M.1
  • 12
    • 0000507937 scopus 로고
    • The stability of ion-molecule complexes of some carboxylates and water have shown little dependence on the hydrogen bond acceptor. Unlike the acetylide-methanol complexes studied here, these complexes are weakly bound (∼13-16 kcal/mol) and the anion and neutral differ in acidity by >30 kcal/mol. Blades, A.; Klassen, J. S.; Kebarle, P. J. Am. Chem. Soc. 1995, 117, 10563-10571.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10563-10571
    • Blades, A.1    Klassen, J.S.2    Kebarle, P.3
  • 13
    • 33646193448 scopus 로고
    • Ph.D. Dissertation, Stanford University, Stanford, CA
    • Wilbur, J. L. Ph.D. Dissertation, Stanford University, Stanford, CA, 1993.
    • (1993)
    • Wilbur, J.L.1
  • 19
    • 33646204980 scopus 로고    scopus 로고
    • note
    • complex The relative values should be more accurate for these structurally similar complexes (0.5 kcal/mol based on experimental error).
  • 20
    • 33646179131 scopus 로고
    • Gaussian, Inc.: Pittsburgh, PA
    • Frisch, M. J.; et al. Ganssian94, RevC.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
    • (1995) Ganssian94, RevC.3
    • Frisch, M.J.1
  • 25
    • 0141917879 scopus 로고    scopus 로고
    • NIST Standard Reference Database 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD
    • Relative acidities were taken from Bartmess, J. E. NIST Chemistry WebBook, NIST Standard Reference Database 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 1998.
    • (1998) NIST Chemistry WebBook
    • Bartmess, J.E.1
  • 28
    • 0033620446 scopus 로고    scopus 로고
    • Clearly, charge distributions may be perturbed in the ion-molecule complex and charge-transfer effects may be important. An electrostatic model does provide a good qualitative model to understand the interaction. Recent experimental work suggests that neutral hydrogen bonds may have partial covalent character. See Cornilescu, G.; et al. J. Am. Chem. Soc. 1999, 121, 2949;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2949
    • Cornilescu, G.1


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