Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR

John Tierney, Douglas Sheridan, Kathy Kovalesky, Linda M. Mascavage, Kimberly Schneider, Carrie Sheely

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Substituents placed on the phenyl rings of 3-benzyl-2-phenyl-1,3-thiazolidin-4-one affect the electron density surrounding both the methine proton, Hm, at C(2), Ha and Hb at C(5), and Hc and Hd at the benzyl carbon. The electron density changes are also exhibited at the C(2), C(4), C(5) and the benzyl carbons. These electron density changes are reflected, respectively, in the differing chemical shifts for the 1H and 13C NMR spectra for these atoms relative to the unsubstituted compound. Correlations for the effects of various substituents in both the 2-phenyl and 3-benzyl rings with the 1H and 13C chemical shifts, for the aforementioned sites, are discussed using Hammett σ constants. The large chemical shift difference observed for the geminal N-benzylic protons, Hc and Hd is discussed.

Original languageEnglish (US)
Pages (from-to)105-111
Number of pages7
JournalHeterocyclic Communications
Volume6
Issue number2
StatePublished - Dec 1 2000

Fingerprint

Chemical shift
Carrier concentration
Nuclear magnetic resonance
Protons
Carbon
Atoms

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Tierney, J., Sheridan, D., Kovalesky, K., Mascavage, L. M., Schneider, K., & Sheely, C. (2000). Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR. Heterocyclic Communications, 6(2), 105-111.
Tierney, John ; Sheridan, Douglas ; Kovalesky, Kathy ; Mascavage, Linda M. ; Schneider, Kimberly ; Sheely, Carrie. / Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR. In: Heterocyclic Communications. 2000 ; Vol. 6, No. 2. pp. 105-111.
@article{9b85880384d74567aed4fe12e4c4637a,
title = "Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR",
abstract = "Substituents placed on the phenyl rings of 3-benzyl-2-phenyl-1,3-thiazolidin-4-one affect the electron density surrounding both the methine proton, Hm, at C(2), Ha and Hb at C(5), and Hc and Hd at the benzyl carbon. The electron density changes are also exhibited at the C(2), C(4), C(5) and the benzyl carbons. These electron density changes are reflected, respectively, in the differing chemical shifts for the 1H and 13C NMR spectra for these atoms relative to the unsubstituted compound. Correlations for the effects of various substituents in both the 2-phenyl and 3-benzyl rings with the 1H and 13C chemical shifts, for the aforementioned sites, are discussed using Hammett σ constants. The large chemical shift difference observed for the geminal N-benzylic protons, Hc and Hd is discussed.",
author = "John Tierney and Douglas Sheridan and Kathy Kovalesky and Mascavage, {Linda M.} and Kimberly Schneider and Carrie Sheely",
year = "2000",
month = "12",
day = "1",
language = "English (US)",
volume = "6",
pages = "105--111",
journal = "Heterocyclic Communications",
issn = "0793-0283",
publisher = "Walter de Gruyter GmbH & Co. KG",
number = "2",

}

Tierney, J, Sheridan, D, Kovalesky, K, Mascavage, LM, Schneider, K & Sheely, C 2000, 'Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR', Heterocyclic Communications, vol. 6, no. 2, pp. 105-111.

Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR. / Tierney, John; Sheridan, Douglas; Kovalesky, Kathy; Mascavage, Linda M.; Schneider, Kimberly; Sheely, Carrie.

In: Heterocyclic Communications, Vol. 6, No. 2, 01.12.2000, p. 105-111.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR

AU - Tierney, John

AU - Sheridan, Douglas

AU - Kovalesky, Kathy

AU - Mascavage, Linda M.

AU - Schneider, Kimberly

AU - Sheely, Carrie

PY - 2000/12/1

Y1 - 2000/12/1

N2 - Substituents placed on the phenyl rings of 3-benzyl-2-phenyl-1,3-thiazolidin-4-one affect the electron density surrounding both the methine proton, Hm, at C(2), Ha and Hb at C(5), and Hc and Hd at the benzyl carbon. The electron density changes are also exhibited at the C(2), C(4), C(5) and the benzyl carbons. These electron density changes are reflected, respectively, in the differing chemical shifts for the 1H and 13C NMR spectra for these atoms relative to the unsubstituted compound. Correlations for the effects of various substituents in both the 2-phenyl and 3-benzyl rings with the 1H and 13C chemical shifts, for the aforementioned sites, are discussed using Hammett σ constants. The large chemical shift difference observed for the geminal N-benzylic protons, Hc and Hd is discussed.

AB - Substituents placed on the phenyl rings of 3-benzyl-2-phenyl-1,3-thiazolidin-4-one affect the electron density surrounding both the methine proton, Hm, at C(2), Ha and Hb at C(5), and Hc and Hd at the benzyl carbon. The electron density changes are also exhibited at the C(2), C(4), C(5) and the benzyl carbons. These electron density changes are reflected, respectively, in the differing chemical shifts for the 1H and 13C NMR spectra for these atoms relative to the unsubstituted compound. Correlations for the effects of various substituents in both the 2-phenyl and 3-benzyl rings with the 1H and 13C chemical shifts, for the aforementioned sites, are discussed using Hammett σ constants. The large chemical shift difference observed for the geminal N-benzylic protons, Hc and Hd is discussed.

UR - http://www.scopus.com/inward/record.url?scp=0034400041&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034400041&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0034400041

VL - 6

SP - 105

EP - 111

JO - Heterocyclic Communications

JF - Heterocyclic Communications

SN - 0793-0283

IS - 2

ER -

Tierney J, Sheridan D, Kovalesky K, Mascavage LM, Schneider K, Sheely C. Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR. Heterocyclic Communications. 2000 Dec 1;6(2):105-111.