NMR and AM1 Quantum Chemical Study of the Regioselectivity of the Reaction of 2-Hydroxyethyl Methacrylate with 3-Nitrophthalic Anhydride

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Title:NMR and AM1 Quantum Chemical Study of the Regioselectivity of the Reaction of 2-Hydroxyethyl Methacrylate with 3-Nitrophthalic Anhydride
Creators:
Kříž, Jaroslav
Dybal, Jiří
Sedláková, Zdeňka
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 1, pp. 69-82
Uncontrolled Keywords:Regioselectivity of esterification, Quantum chemistry, NMR

Abstract

The reaction of 2-hydroxyethyl methacrylate with 3-nitrophthalic anhydride catalyzed with triethylamine results in the 3 : 1 mixture of two possible monoesters, the more populated one being that with the ester group in ortho position to the nitro group. The isomers were identified and quantified by <sup>1</sup>H and <sup>13</sup>C 1D and 2D techniques including APT, INEPT, superselective long-range (SSLR) INEPT, SSLR HHCR, COSY, NOESY, HETCOR and COLOC. Theoretical analysis was done on the model reaction of methanol with the anhydride using semiempirical AM1 quantum chemical calculations. The results indicate that the relative regioselectivity of the reaction is due to both the electron distribution in the anhydride molecule and hydrogen bonding in the stages immediately preceding the transition state.

Title:NMR and AM1 Quantum Chemical Study of the Regioselectivity of the Reaction of 2-Hydroxyethyl Methacrylate with 3-Nitrophthalic Anhydride
Creators:
Kříž, Jaroslav
Dybal, Jiří
Sedláková, Zdeňka
Uncontrolled Keywords:Regioselectivity of esterification, Quantum chemistry, NMR
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:1
Page Range:pp. 69-82
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19970069UNSPECIFIED
ID Code:1096
Item Type:Article
Deposited On:06 Feb 2009 17:06
Last Modified:06 Feb 2009 16:06

Citation

Kříž, Jaroslav; Dybal, Jiří; Sedláková, Zdeňka (1997) NMR and AM1 Quantum Chemical Study of the Regioselectivity of the Reaction of 2-Hydroxyethyl Methacrylate with 3-Nitrophthalic Anhydride. Collection of Czechoslovak Chemical Communications, 62 (1). pp. 69-82. ISSN 0010-0765

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