A Síntese Homoquiral da Alanina: Avaliação do Caminho Reacional Através de Métodos de Estrutura Eletrônica

Matheus  A. R. N. Silva; Valter  H. Carvalho-Silva

doi:10.19142/rpq.v17i31.653

Matheus A. R. N. Silva Divisão de Modelagem de Transformações Físicas e Químicas, Grupo de Química Teórica e Estrutural, Universidade Estadual de Goiás, Anápolis/GO.
Valter H. Carvalho-Silva Divisão de Modelagem de Transformações Físicas e Químicas, Grupo de Química Teórica e Estrutural, Universidade Estadual de Goiás, Anápolis/GO.

DOI: https://doi.org/10.19142/rpq.v17i31.653

Palavras-chave: Alanina, Homoquiralidade, Isomeria E/Z, MP2

Resumo

Com o objetivo de contribuir para uma compreensão mais profunda da homoquiralidade, este trabalho investigou 8 rotas possíveis para a síntese
homoquiral da Alanina. Em 4 reações, os compostos de partida E-etanimina e Z-etanimina foram estudados reagindo com monóxido de carbono e avaliando-se a formação dos estereocentros R e S para intermediários da síntese da alanina. Em outras 4 reações, as etaniminas foram postas a reagir com dióxido de carbono, também se analisando a formação dos estereocentros quirais. Calculou-se então as estruturas moleculares e as energias dos estados estacionários (reagentes, produtos, complexos de van der Waals e estados de transição) dessas reações. Constatou-se
o favorecimento das reações com o isômero Z das iminas, bem como das reações envolvendo CO. Porém, não houve identificação de canais preferenciais para a formação dos centros quirais R ou S da Alanina indicando que o processo de homoquiralidade pode estar relacionado a efeitos dinâmicos no processo reativo.

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