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1990•Angewandte Chemie International Edition in EnglishRequires access

Dependence of Anomeric Stabilization on Structure in Acetals

Hans‐Dieter Beckhaus, Barbara Dogan, Johannes Hädrich, Christoph Rüchardt, Sergej Verevkin

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Abstract

Quantitative statements about the anomeric effect in acetals 1 were possible through group increments which were derived for the key-C-atom by comparison of the bonding enthalpies in acetals, ethers, and hydrocarbons. The extra stabilization by the second oxygen substituent is surprisingly large and is strongly substituent-dependent [(alkylphe-nylketoneacetal −12.1, formaldehydeacetal −3.3 kcal mol−1)].

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What this paper is about

Quantitative statements about the anomeric effect in acetals 1 were possible through group increments which were derived for the key-C-atom by comparison of the bonding enthalpies in acetals, ethers, and hydrocarbons. The extra stabilization by the second oxygen substituent is surprisingly large and is strongly substituent-dependent [(alkylphe-nylketoneacetal −12.1, formaldehydeacetal −3.3 kcal mol−1)].

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Available abstract

Quantitative statements about the anomeric effect in acetals 1 were possible through group increments which were derived for the key-C-atom by comparison of the bonding enthalpies in acetals, ethers, and hydrocarbons. The extra stabilization by the second oxygen substituent is surprisingly large and is strongly substituent-dependent [(alkylphe-nylketoneacetal −12.1, formaldehydeacetal −3.3 kcal mol−1)].

Key concepts: Substituent, Anomer, Chemistry, Anomeric effect, Oxygen atom, Atom (system on chip), Oxygen, Computational chemistry

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