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Synthesis and Crystal Structures of Three Thioether Functionalized Formamidines and Their Corresponding Lithium Formamidinates
Author(s) -
Fink Matthias J. U.,
Heiser Christian,
Wagner Christoph,
Merzweiler Kurt
Publication year - 2022
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.202200122
Subject(s) - thioether , lithium (medication) , crystal structure , chemistry , intramolecular force , hydrogen bond , derivative (finance) , amidine , stereochemistry , crystallography , crystal (programming language) , medicinal chemistry , molecule , organic chemistry , medicine , computer science , financial economics , programming language , economics , endocrinology
Three thioether functionalized formamidines RNHC(H)NR (R=2‐SMe‐C 6 H 4 , 2‐S t Bu‐C 6 H 4 , 2‐SPh‐C 6 H 4 ) were prepared from the corresponding amines RNH 2 and triethyl orthoformate. X‐ray crystal structure determinations revealed the typical E configuration about the amidine C=N bond for all three compounds. The 2‐SMe and 2‐S t Bu derivatives exhibit the most frequently observed anti orientation of the RNH group while the 2‐SPh derivative displays the much more rarely encountered syn arrangement. All three compounds exhibit weak intramolecular N−H⋅⋅⋅S hydrogen bridges of theS 1 1 ${{S}_{1}^{1}}$ (5) type. Treatment of the amidines with n ‐BuLi led to the formation of the corresponding lithium amidinates. X‐ray crystal structure determinations of the lithium amidinates revealed several molecular patterns ranging from the mononuclear complex [Li{2‐S t Bu‐C 6 H 4 N) 2 CH} 2 (THF) 2 ] to the trimeric compound [Li 3 {(2‐SMe‐C 6 H 4 N) 2 CH} 3 ].