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Volumn 71, Issue 6, 2006, Pages 2373-2383

Is [N+-H⋯O] hydrogen bonding the most important noncovalent interaction in macrocycle-dibenzylammonium ion complexes?

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; BENZENE; BONDING; CARBOXYLIC ACIDS; ETHYLENE; GLYCOLS; HYDROGEN; MOLECULES; PHENOLIC RESINS; SYNTHESIS (CHEMICAL);

EID: 33645030407     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052411+     Document Type: Article
Times cited : (39)

References (94)
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  • 8
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    • Hiraoka, M., Ed.; Elsevier: Amsterdam. The Netherlands
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    • (1992) Crown Ethers and Analogous Compounds
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    • (2001) Molecular Switches
  • 50
    • 0034703739 scopus 로고    scopus 로고
    • The interaction energies of benzene-methane (C-H⋯π) and benzene-ammonia (N-H⋯π) complexes have been calculated to be -1.45 and -2.22 kcal/mol, respectively; i.e., ca. 30-40% of the hydrogen bonding energy of the water dimer. See: (c) Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2000, 122, 11450-11458.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11450-11458
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  • 54
    • 0003914038 scopus 로고    scopus 로고
    • Oxford University Press: New York
    • The strength of a hydrogen bonding interaction depends on the characteristics of the donor and acceptor as well as their environment, but generally it ranges between 1 and 5 kcal/mol. For detailed descriptions of hydrogen bonding interaction, see: (a) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
    • (1997) An Introduction to Hydrogen Bonding
    • Jeffrey, G.A.1
  • 56
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    • 4 with an F atom adds ca. 1 kcal/mol to the binding energy. See: (a) Novoa, J. J.; Mota, F. Chem. Phys. Lett. 1997, 266, 23-30.
    • (1997) Chem. Phys. Lett. , vol.266 , pp. 23-30
    • Novoa, J.J.1    Mota, F.2
  • 66
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    • note
    • 3 to the reaction mixture did not increase the yield significantly, suggesting that the templating effects of these alkali metal ions are very weak in these macrocyclization reactions.
  • 73
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    • note
    • + ion and macrocycle 1b, relative to that of macrocycle 1a. Shielding of the ammonium center by the macrocycle has been suggested as an important factor in the success of these stoppering reactions; see ref 33.
  • 74
    • 0037165719 scopus 로고    scopus 로고
    • A similar method had been applied previously to prove the structural integrity of rotaxanes; see: Chiu, S.-H.; Stoddart, J. F. J. Am. Chem. Soc. 2002, 124, 4174-4175.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4174-4175
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  • 84
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    • + ion and BMP26C8 is also negligible; see refs 13 and 16. When applying the concept of multivalency, however, DB24C8 can interact quite strongly with bipyridinium ions in solution; see: Badjiæ, J. D.; Cantrill, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 2004, 126, 2288-2289.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 2288-2289
    • Badjiæ, J.D.1    Cantrill, S.J.2    Stoddart, J.F.3
  • 94
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    • Program for the Refinement of Crystal Structures; University of Gottingen: Gottingen, Germany
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.