Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies

S. M. Neugebauer Crawford; A. N. Taha; N. S. True; C. B. LeMaster

doi:10.1021/jp970953s

Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies

S. M. Neugebauer Crawford
, A. N. Taha
, N. S. True
, C. B. LeMaster

Chemistry Department

University of California at Davis

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

28 Scopus citations

Abstract

Temperature-dependent gas-phase ¹H NMR spectra of seven thiocarbonyl-substituted N,N-dimethylthioamides (YCSN(CH₃)₂) obtained at 300 MHz are consistent with the following free activation energies ΔG^‡₂₉₈ (kcal mol^-1): Y = H, 22.5 (0.1); CH₃, 18.0 (0.1); F, 18.3 (0.1); Cl, 16.9 (0.2); CF₃, 17.2 (0.1); CH₂CH₃, 17.6 (0.1); CH(CH₃)₂, 16.3 (0.1). The results are compared to condensed-phase values and to the corresponding gas-phase oxoamides.

Original language	English
Pages (from-to)	4699-4706
Number of pages	8
Journal	Journal of Physical Chemistry A
Volume	101
Issue number	26
DOIs	https://doi.org/10.1021/jp970953s
State	Published - 26 Jun 1997

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title = "Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies",

abstract = "Temperature-dependent gas-phase 1H NMR spectra of seven thiocarbonyl-substituted N,N-dimethylthioamides (YCSN(CH3)2) obtained at 300 MHz are consistent with the following free activation energies ΔG‡298 (kcal mol-1): Y = H, 22.5 (0.1); CH3, 18.0 (0.1); F, 18.3 (0.1); Cl, 16.9 (0.2); CF3, 17.2 (0.1); CH2CH3, 17.6 (0.1); CH(CH3)2, 16.3 (0.1). The results are compared to condensed-phase values and to the corresponding gas-phase oxoamides.",

author = "\{Neugebauer Crawford\}, \{S. M.\} and Taha, \{A. N.\} and True, \{N. S.\} and LeMaster, \{C. B.\}",

year = "1997",

month = jun,

day = "26",

doi = "10.1021/jp970953s",

language = "English",

volume = "101",

pages = "4699--4706",

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TY - JOUR

T1 - Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies

AU - Neugebauer Crawford, S. M.

AU - Taha, A. N.

AU - True, N. S.

AU - LeMaster, C. B.

PY - 1997/6/26

Y1 - 1997/6/26

N2 - Temperature-dependent gas-phase 1H NMR spectra of seven thiocarbonyl-substituted N,N-dimethylthioamides (YCSN(CH3)2) obtained at 300 MHz are consistent with the following free activation energies ΔG‡298 (kcal mol-1): Y = H, 22.5 (0.1); CH3, 18.0 (0.1); F, 18.3 (0.1); Cl, 16.9 (0.2); CF3, 17.2 (0.1); CH2CH3, 17.6 (0.1); CH(CH3)2, 16.3 (0.1). The results are compared to condensed-phase values and to the corresponding gas-phase oxoamides.

AB - Temperature-dependent gas-phase 1H NMR spectra of seven thiocarbonyl-substituted N,N-dimethylthioamides (YCSN(CH3)2) obtained at 300 MHz are consistent with the following free activation energies ΔG‡298 (kcal mol-1): Y = H, 22.5 (0.1); CH3, 18.0 (0.1); F, 18.3 (0.1); Cl, 16.9 (0.2); CF3, 17.2 (0.1); CH2CH3, 17.6 (0.1); CH(CH3)2, 16.3 (0.1). The results are compared to condensed-phase values and to the corresponding gas-phase oxoamides.

UR - https://www.scopus.com/pages/publications/0041836665

U2 - 10.1021/jp970953s

DO - 10.1021/jp970953s

M3 - Article

AN - SCOPUS:0041836665

SN - 1089-5639

VL - 101

SP - 4699

EP - 4706

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

IS - 26

ER -

Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies

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