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Structure and Bonding in Bis(1‐naphthyl) Diselenide and Bis{[2‐( N , N ‐dimethylamino)methyl]phenyl} Tetraselenide, and Their Brominated Derivatives
Author(s) -
Takaluoma Esther M.,
Takaluoma Teemu T.,
Oilunkaniemi Raija,
Laitinen Risto S.
Publication year - 2015
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201500043
Subject(s) - diselenide , chemistry , medicinal chemistry , halogenation , bromide , monomer , nuclear magnetic resonance spectroscopy , crystal structure , diphenyl diselenide , allyl bromide , stereochemistry , organic chemistry , selenium , polymer
The formation and crystal structures of bis(1‐naphthyl) diselenide ( 1 ) and bis{[2‐( N , N ‐dimethylamino)methyl]phenyl} tetraselenide ( 2 ) are described. Whereas 1 can be produced in good yields, 2 is formed only as a minor product together with the known main product, bis{[2‐( N , N ‐dimethylamino)methyl]phenyl} diselenide. The composition of the reaction mixture is semi‐quantitatively estimated by 77 Se NMR spectroscopy and DFT calculations. The effect of the n 2 →σ*(Se–Se) and π→σ*(Se–Se) secondary bonding interactions on the Se–Se bonds is discussed both by DFT calculations and comparison with literature, as available. The bromination of 1 yields monomeric (1‐naphthyl)selenenyl bromide ( 3 ) in good yields. That of the reaction mixture of (C 6 H 4 CH 2 NMe 2 )Se x ( x = 2–4) and Se 8 afforded (C 6 H 4 CH 2 NMe 2 H) 2 [SeBr 4 ] ( 4 ) and (C 6 H 4 CH 2 NMe 2 H) 2 [SeBr 6 ] ( 5 ) in addition to (C 6 H 4 CH 2 NMe 2 )SeBr, which has been previously reported.