Estereocentro

Estereocentro ou centro estereogênico é qualquer átomo em uma molécula em que os grupos tais que o intercambiamento dos grupos conduz a um estereoisômero ^[1]. Em química orgânica isto usualmente se refere a um átomo de carbono, fósforo ou enxofre, embora também seja possível que outros átomos sejam estereocentros, tanto em química orgânica como em química inorgânica. é muitas vezes confundido com o conceito de centro quiral, que é um ponto (átomo) que está ligado a quatro substituintes diferentes. Logo, realizando-se a operaçäo de simetria inversão (i ou S2) nesse ponto, obtém-se o enantiômero (imagem especular) da molécula original. ^[2]

Uma molécula pode ter múltiplos estereocentros, resultando em muitos estereoisômeros. Em compostos no qual o estereoisomerismo é devido a centros estereogênicos tetraédricos, o número total de estereoisômeros hipoteticamente possíveis não irá exceder 2ⁿ, onde n é o número de estereocentros tetrahédricos. Moléculas com simetria frequentemente tem menos que o número máximo possível de estereoisômeros.

O termo estereocentro foi introduzido em 1984 por Mislow e Siegel ^[3].

O conceito de estereocentro é frequentemente confundido com o conceito mais restrito de centro de quiralidade. É importante lembrar que um composto como 2-buteno tem dois estereocentros formando dois possíveis estereoisômeros (cis e trans 2-buteno) (e não 4!) e não é considerado um composto meso ^[4]

Referências

↑ Solomons & Fryhle. (2004). Organic Chemistry, 8th ed.
↑ IUPAC Gold Book: "chirality centre"
↑ Stereoisomerism and local chirality Kurt Mislow and Jay Siegel J. Am. Chem. Soc.; 1984; 106(11) pp 3319 - 3328; doi:10.1021/ja00323a043
↑ Precision in Stereochemical Terminology Wade, LeRoy G., Jr. J. Chem. Educ. 2006 83 1793 Link.

Ver também

Isomeria geométrica

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