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Direct observation of a photoinduced nonstabilized nitrile imine structure in the solid state.

ABSTRACT: We report the direct observation of a bent geometry for a nonstabilized nitrile imine in a metal-coordination crystal. The photoinduced tetrazole ring rupture to release N(2) appears to depend on the size of voids around the N(3)-N(4) bond in the crystal lattice. We further observed the selective formation of the 1,3-addition product when a reactive nitrile imine was photogenerated in water. Overall, the bent nitrile imine geometry agrees with the 1,3-dipolar structure, a transient reactive species that mediates the photoinduced 1,3-dipolar cycloaddition in the aqueous medium.

SUBMITTER: Zheng SL

PROVIDER: S-EPMC2797338 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Direct observation of a photoinduced nonstabilized nitrile imine structure in the solid state.

Zheng Shao-Liang SL Wang Yizhong Y Yu Zhipeng Z Lin Qing Q Coppens Philip P

Journal of the American Chemical Society 20091201 50

We report the direct observation of a bent geometry for a nonstabilized nitrile imine in a metal-coordination crystal. The photoinduced tetrazole ring rupture to release N(2) appears to depend on the size of voids around the N(3)-N(4) bond in the crystal lattice. We further observed the selective formation of the 1,3-addition product when a reactive nitrile imine was photogenerated in water. Overall, the bent nitrile imine geometry agrees with the 1,3-dipolar structure, a transient reactive spec ...[more]

PMID: 19928921

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