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Determination of substitution sites in monosubstituted five-membered aromatic heterocycles

✍ Scribed by Jan Schraml; Roman Kubec; Petra Kučerová

Book ID
102525973
Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
144 KB
Volume
49
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Similar magnitudes of proton–proton couplings across three, four, and five bonds and proton–carbon couplings across two and three bonds combined with difficult to predict substituent effects make the results of an indiscriminate use of routine (COSY, HSQC, HMBC, etc.) techniques for substitution site determination in C‐monosubstituted five‐membered heteroaromatics suspect. As demonstrated on two examples of natural products, the use of 1,1‐ADEQUATE leads to unambiguous substitution site determination lending thus further support to suggested inclusion of 1,1‐ADEQUATE data into computer‐assisted structure elucidation (CASE) protocols. Copyright © 2011 John Wiley & Sons, Ltd.

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## Abstract The GIAO (Gauge Including Atomic Orbitals) DFT (Density Functional Theory) method is applied at the B3LYP/6–31+G(d,p)//B3LYP/6–31+G(d), B3LYP/6–311++G(d,p)//B3LYP/6–31+G(d), B3LYP/6–311+G (2d,p)//B3LYP/6–31+G(d) and B3LYP/6–311++G(d,p)//B3LYP/6–311++G(d,p) levels of theory for the calcu