An Analysis of Substituent Effects on the Proton and Carbon-13 Chemical Shifts of 2-Substituted 9-Isothiocyanatoacridines

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Title:An Analysis of Substituent Effects on the Proton and Carbon-13 Chemical Shifts of 2-Substituted 9-Isothiocyanatoacridines
Creators:
Danihel, Ivan
Imrich, Ján
Kristian, Pavol
Liptaj, Tibor
Mazagová, Dana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 8, pp. 1833-1840

Abstract

<p>Proton and <sup>13</sup>C NMR chemical shifts and coupling constants <i>J</i>(H,H) of a series of 2-substituted 9-isothiocyanatoacridines and their 4-methyl and 4-methoxy analogs were determined. The obtained values were utilized in analysis of substituent effects using empirical equations based on two- and three-parameter linear correlations. It was found that short-range interactions (positions <i>ipso</i>, <i>ortho</i> and <i>meta</i>) are well described by the three-parameter model of Reynolds whereas long-range effects are satisfactorily compatible with the two-parameter model. The dominant direction of conjugation in the acridine skeleton was derived from changes in chemical shifts due to substitution (SCS).

Title:An Analysis of Substituent Effects on the Proton and Carbon-13 Chemical Shifts of 2-Substituted 9-Isothiocyanatoacridines
Creators:
Danihel, Ivan
Imrich, Ján
Kristian, Pavol
Liptaj, Tibor
Mazagová, Dana
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:59
Number:8
Page Range:pp. 1833-1840
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19941833UNSPECIFIED
ID Code:607
Item Type:Article
Deposited On:06 Feb 2009 17:02
Last Modified:06 Feb 2009 16:02

Citation

Danihel, Ivan; Imrich, Ján; Kristian, Pavol; Liptaj, Tibor; Mazagová, Dana (1994) An Analysis of Substituent Effects on the Proton and Carbon-13 Chemical Shifts of 2-Substituted 9-Isothiocyanatoacridines. Collection of Czechoslovak Chemical Communications, 59 (8). pp. 1833-1840. ISSN 0010-0765

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