2003-06-01, English, Article, Journal or magazine article edition: Variation of the ease of [alpha]-sulfonyl carbanion formation with the orientation of different [beta]-substituents: experimental evidence for the generality of negative hyperconjugation as an important substituent effect.(Author Abstract) King, James F.; Li, Manqing; Cheng, Allan Zijun; ...

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Physical Description
  • Author Abstract
  • Magazine/​Journal article
Published
  • NRC Research Press, 2003 June
Language
  • English

Edition details

Title
  • Variation of the ease of [alpha]-sulfonyl carbanion formation with the orientation of different [beta]-substituents: experimental evidence for the generality of negative hyperconjugation as an important substituent effect.(Author Abstract)
Also Titled
  • Variation of the ease of [alpha]-sulfonyl carbanion formation with the orientation of different [beta]-substituents: experimental evidence for the generality of negative hyperconjugation as an important substituent effect.
Appears In
  • Canadian Journal of Chemistry, v.81, no.6, 2003 June, p.638(9) (ISSN: 0008-4042)
Author
  • King, James F.
  • Li, Manqing
  • Cheng, Allan Zijun
  • Dave, Vinod
  • Payne, Nicholas C.
Published
  • NRC Research Press, 2003 June
Physical Description
  • Author Abstract
  • Magazine/​Journal article
Subjects
Target Audience
  • Academic
Summary
  • Following up on our previous observation that the rate of formation of a [beta]-alkoxy-substituted [alpha]-sulfonyl carbanion depends on the stereochemistry of the alkoxy group, we have found similar behaviour when the [beta]-substituent is [R.sub.2]N, RS, or [R.sub.3][N.sup.+]. With each substituent, the variation of [k.sub.N] (defined by [k.sub.N] =​ ([k.sub.exch])X.sup./​[([k.sub.exch]).sub.model]) is consistent with an equation of the form log [[k.sub.N]] =​ a + b [cos.sup.2][theta] where [theta] is the H-C-C-X torsion angle. We propose that the a term describes the polar (field plus inductive) effect and the b term the negative hyperconjugative effect of the substituent; we show how the variations in a and b may be readily accommodated within this framework. Some features of the trialkylammonio group previously postulated in the literature are discussed in the light of our results. Key words: negative hyperconjugation, substituent effects, stereoelectronic factors, sulfonyl carbanions, anomeric effect.
Terms of Use
  • COPYRIGHT 2003 NRC Research Press
Language
  • English
Database
  • Gale Academic OneFile
  • Gale General OneFile
  • Gale Expanded Academic
Identifier
  • 109178884

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Macquarie University. Macquarie University Library. Open to the public 992055610802171; QD1 .C285; Vol. 29 (1951)-vol. 33 (1955); vol. 39 (1961)-vol. 83, no. 8 (2005); vol. 83, no. 10 (2005)-vol. 83, no. 12 (2005) Periodical; Journal, magazine, other English; French
NSW Department of Industry. DTIRIS: Electronic Resources Library. Not open to the public V 29 1951 - V 75 1997 Periodical; Journal, magazine, other English; French
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University of Newcastle. University of Newcastle Library. Open to the public 540.5/9; Vol. 29, no. 1-v. 75, no. 12; Jan. 1951-Dec. 1997 Periodical; Journal, magazine, other English; French
University of New England. Dixson Library. Open to the public 1024-67060; <1024-67060>; P540.5/CAN <1024-67060>; V.29 (1951)- Periodical; Journal, magazine, other English; French
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Western Sydney University. Campbelltown Campus Library. Open to the public 9919157280001571; HELD; Vol. 62, no. 7 (1984) - v. 74 (1996)[Impf.]. Periodical; Journal, magazine, other English; French
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Monash University. Monash University Library. Open to the public 99867301751; 540.5 C212; v. 29 (1951) to v.84 (2006) ; Incomplete ; Includes Indexes; Lacks: v. 52 (1974) ; v. 53, no. 1-6 (1975) ; v. 53, no. 13-24 (1975) ; v.54 (1976) to v. 55 (1977) ; v. 73 (1995) to v. 77 (1999); OS; YOS-SER Periodical; Journal, magazine, other English; French
RMIT University. RMIT University Library. Open to the public 9912892330001341; PER 540 C212; Incomplete. Held in Storage. Request from <a href=http://www.rmit.edu.au/library/dds target=_blank>Document Delivery</a>; v. 51, no. 1 (Jan. 1, 1973)-v. 70, no. 12 (Dec. 1992) Periodical; Journal, magazine, other English; French
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