New example of a symmetric NHN hydrogen bond in protonated 1,8-bis(dimethylamino)naphthalene (DMAN)

Add time:08/22/2019    Source:sciencedirect.com

The crystal structure of the adduct of 1,8-bis(dimethylamino)naphthalene (DMAN) with tetrazole (DMAN-THM), containing crystallographically symmetric NHN+ hydrogen bridges, was determined. The crystals of DMAN-THM (monohydrate) are orthorhombic, space group Pnma, with Z = 4, a = 9.500(3), b = 10.966(5), c = 15.615(4) Å, R(N⋯N) = 2.573(2), r(NH) = 1.312(5) Å and ∢ NHN = 157(2)°. The symmetry of the DMAN·H+ cations is reflected in an equivalence of the two moieties of the naphthyl ring. In the infrared spectra, the low-frequency ν(NHN) band centred at about 500 cm−1 (half-width of abouth 250 cm−1) is observed, typical of very strong NHN hydrogen bonds.

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