Estimation of the chemical shifts of olefinic protons using additive increments-III. Examples of utility in NMR studies and the identification of some structural features responsible for deviations from additivity

U. E. Matter; C. Pascual; E. Pretsch; A. Pross; W. Simon; S. Sternhell

doi:10.1016/S0040-4020(01)82823-4

Estimation of the chemical shifts of olefinic protons using additive increments-III. Examples of utility in NMR studies and the identification of some structural features responsible for deviations from additivity

U. E. Matter, C. Pascual, E. Pretsch, A. Pross, W. Simon, S. Sternhell

Research output: Contribution to journal › Article › peer-review

71 Scopus citations

Abstract

Examples of utilization of the additive shielding parameters for olefinic protons in making NMR assignments are given and modifications of some published data are suggested. The role of ground-state mesomeric effects on chemical shifts in numerous classes of alkenes is stressed. Some structural features associated with significant deviations from results calculated on the basis of the additivity principle are: (i) unusual juxtaposition of remote functional groups, (ii) planar conjugated carbonyl derivatives, (iii) bicyclic olefins and dienes, (iv) vinyl ethers in which the lone pairs on the oxygen are constrained into certain conformations, (v) vinyl iodides.

Original language	English
Pages (from-to)	2023-2034
Number of pages	12
Journal	Tetrahedron
Volume	25
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4020(01)82823-4
State	Published - 1 Jan 1969
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Matter, U. E., Pascual, C., Pretsch, E., Pross, A., Simon, W., & Sternhell, S. (1969). Estimation of the chemical shifts of olefinic protons using additive increments-III. Examples of utility in NMR studies and the identification of some structural features responsible for deviations from additivity. Tetrahedron, 25(9), 2023-2034. https://doi.org/10.1016/S0040-4020(01)82823-4

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abstract = "Examples of utilization of the additive shielding parameters for olefinic protons in making NMR assignments are given and modifications of some published data are suggested. The role of ground-state mesomeric effects on chemical shifts in numerous classes of alkenes is stressed. Some structural features associated with significant deviations from results calculated on the basis of the additivity principle are: (i) unusual juxtaposition of remote functional groups, (ii) planar conjugated carbonyl derivatives, (iii) bicyclic olefins and dienes, (iv) vinyl ethers in which the lone pairs on the oxygen are constrained into certain conformations, (v) vinyl iodides.",

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Matter, UE, Pascual, C, Pretsch, E, Pross, A, Simon, W & Sternhell, S 1969, 'Estimation of the chemical shifts of olefinic protons using additive increments-III. Examples of utility in NMR studies and the identification of some structural features responsible for deviations from additivity', Tetrahedron, vol. 25, no. 9, pp. 2023-2034. https://doi.org/10.1016/S0040-4020(01)82823-4

Estimation of the chemical shifts of olefinic protons using additive increments-III. Examples of utility in NMR studies and the identification of some structural features responsible for deviations from additivity. / Matter, U. E.; Pascual, C.; Pretsch, E. et al.
In: Tetrahedron, Vol. 25, No. 9, 01.01.1969, p. 2023-2034.

Research output: Contribution to journal › Article › peer-review

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T1 - Estimation of the chemical shifts of olefinic protons using additive increments-III. Examples of utility in NMR studies and the identification of some structural features responsible for deviations from additivity

AU - Matter, U. E.

AU - Pascual, C.

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AU - Pross, A.

AU - Simon, W.

AU - Sternhell, S.

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AB - Examples of utilization of the additive shielding parameters for olefinic protons in making NMR assignments are given and modifications of some published data are suggested. The role of ground-state mesomeric effects on chemical shifts in numerous classes of alkenes is stressed. Some structural features associated with significant deviations from results calculated on the basis of the additivity principle are: (i) unusual juxtaposition of remote functional groups, (ii) planar conjugated carbonyl derivatives, (iii) bicyclic olefins and dienes, (iv) vinyl ethers in which the lone pairs on the oxygen are constrained into certain conformations, (v) vinyl iodides.

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Estimation of the chemical shifts of olefinic protons using additive increments-III. Examples of utility in NMR studies and the identification of some structural features responsible for deviations from additivity

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