메뉴 건너뛰기




Volumn 6, Issue 24, 2000, Pages 4451-4460

Entropy-driven hydrogen bonding: Stereodynamics of a protonated, N,N-chiral "proton sponge"

Author keywords

Hydrogen bonds; Isotopic labeling; NMR spectropscopy; Proton sponges; Stereodynamics

Indexed keywords

NAPHTHALENE DERIVATIVE;

EID: 0034671224     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001215)6:24<4451::AID-CHEM4451>3.0.CO;2-H     Document Type: Article
Times cited : (33)

References (51)
  • 1
    • 85037461779 scopus 로고    scopus 로고
    • note
    • -1.
  • 4
    • 84990134893 scopus 로고
    • Reviews: a) H. A. Staab, T. Saupe, Angew. Chem. 1988, 100, 895; Angew. Chem. Int. Ed. Engl. 1988, 27, 865-879;
    • (1988) Angew. Chem. , vol.100 , pp. 895
    • Staab, H.A.1    Saupe, T.2
  • 5
    • 84990134893 scopus 로고
    • Reviews: a) H. A. Staab, T. Saupe, Angew. Chem. 1988, 100, 895; Angew. Chem. Int. Ed. Engl. 1988, 27, 865-879;
    • (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 865-879
  • 7
    • 0030632978 scopus 로고    scopus 로고
    • C. L. Perrin, J. B. Nielson, Ann. Rev. Phys. Chem. 1997, 48, 511-544; C. L. Perrin, J. B. Nielson, Y. J. Kim, Ber. Bunsenges. Phys. Chem. 1998, 102, 403-409.
    • (1997) Ann. Rev. Phys. Chem. , vol.48 , pp. 511-544
    • Perrin, C.L.1    Nielson, J.B.2
  • 17
    • 85037482569 scopus 로고    scopus 로고
    • note
    • + and proposed that the high basicity of 1a versus 1b is more likely to be due to relief of the steric strain present in 1a and not the formation of hydrogen bonds with very different strength. Based on the data presented herein, we draw a similar conclusion.
  • 18
    • 0000995427 scopus 로고    scopus 로고
    • a = 0 condition is not special). For discussion see: K. N. Houk, J. Org. Chem. 1998, 63, 4611-4619.
    • (1998) J. Org. Chem. , vol.63 , pp. 4611-4619
    • Houk, K.N.1
  • 24
    • 85037476844 scopus 로고
    • see reference [5] in F. Hibbert, H. J. Robbins
    • A value of 0.9 has been reported by A. J. Kresge et al., see reference [5] in F. Hibbert, H. J. Robbins, Chem. Commun. 1980, 141-142.
    • (1980) Chem. Commun. , pp. 141-142
    • Kresge, A.J.1
  • 32
    • 85037474293 scopus 로고    scopus 로고
    • note
    • + and compatibility with 2.
  • 33
    • 0003909854 scopus 로고
    • Wiley, Chichester
    • For a discussion of systematic errors and inaccuracies in DNMR see, for example : a) H. Günther, in NMR spectroscopy, 2nd ed., Wiley, Chichester, 1995;
    • (1995) NMR Spectroscopy, 2nd Ed.
    • Günther, H.1
  • 35
    • 85037459907 scopus 로고    scopus 로고
    • note
    • Single crystals were powdered in the bottom of the NMR tube with the end of a glass capillary that had been rounded by melting. Care was taken so that grinding in the solid state would not induce thermal equilibration. The NMR tube was then immersed in an octane-dry ice cooling bath, solvent added and the rounded capillary used to agitate the mixture until dissolution was complete.
  • 36
    • 85037449761 scopus 로고    scopus 로고
    • note
    • - which is fully equilibrated as it is generated. Any water in the reaction system at the start is sequestered by precipitation with the salt and thus in the latter stages of reaction the system is essentially anhydrous.
  • 38
    • 85037460377 scopus 로고    scopus 로고
    • note
    • + and 1. However, the measurement was complicated by a side reaction that resulted in extensive debenzylation.
  • 39
    • 85037485927 scopus 로고    scopus 로고
    • note
    • Evidently, the diastereoisomers cannot directly interconvert since the hydrogen bond must be broken before or during the process and then reformed. In other words the hydrogen is acting as a lock (albeit inefficient). See also reference [30].
  • 42
    • 85037470431 scopus 로고    scopus 로고
    • note
    • We are still trying to prepare 6. However, thus far eight different synthetic routes have been devised and tested. All have proved unsuccessful and this attests to the steric congestion of such a system.
  • 45
  • 46
    • 85037485796 scopus 로고    scopus 로고
    • note
    • [12].
  • 47
    • 85037473125 scopus 로고    scopus 로고
    • note
    • [8]
  • 51
    • 84888886156 scopus 로고    scopus 로고
    • Leipold Associates, USA
    • Commercial software (Leipold Associates, USA).
    • Commercial Software


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.