Structure of 2-amino-5-methylthiazoline and its N-methyl derivatives

Martem'yanova, N. A.; Chunaev, Yu. M.; Przhiyalgovskaya, N. M.; Kurkovskaya, L. N.; Filipenko, O. S.; Алдошин, С. М.

doi:10.1007/bf00531516

Cited by 7 publications

(10 citation statements)

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“…In addition, a search of the Cambridge Structural Database (CSD Version 5.39, November 2017 + 3 updates; Groom et al, 2016) yielded six hits for 2-thiazolidiniminium compounds, with four of them reporting essentially the same cation [CSD refcodes WILBIC (Marthi et al, 1994), WILBOI (Marthi et al, 1994), WILBOI01 (Marthi et al, 1994), YITCEJ (Martem'yanova et al, 1993a), YITCAF (Martem'yanova et al, 1993b) and YOPLUK (Marthi et al, 1995)]. In all cases, the 3-N atom carries a C substituent not N as found in the title compound.…”

Section: Database Surveymentioning

confidence: 99%

“…The system of hydrogen bonds connecting two cations and two anions into 12-membered rings is identical in the racemic and in the optically active crystals. YITCEJ (Martem'yanova et al, 1993a) is a product of the interaction of 2-amino-5-methylthiazoline with methyl iodide, with alkylation at the endocylic N atom, while YITCAF (Martem'yanova et al, 1993b) is a product of the reaction of 3-nitro-5-methoxy-, 3-nitro-5chloro-and 3-bromo-5-nitrosalicylaldehyde with the heterocyclic base to form the salt-like complexes.…”

Section: Figurementioning

confidence: 99%

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Crystal structure and Hirshfeld surface analysis of (E)-5-phenyl-3-[(pyridin-4-ylmethylidene)amino]thiazolidin-2-iminium bromide monohydrate

et al. 2018

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Section: Database Surveymentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-5-phenyl-3-[(pyridin-4-ylmethylidene)amino]thiazolidin-2-iminium bromide monohydrate

et al. 2018

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“…Cg4 and Cg5 are the centroids of the major and minor components of the disordered phenyl ring, respectively. (Marthi et al, 1994), WILBOI (Marthi et al, 1994), WILBOI01 (Marthi et al, 1994), YITCEJ (Martem'yanova et al, 1993a), YITCAF (Martem'yanova et al, 1993b) and YOPLUK (Marthi et al, 1995). The structure of BOBWIB (Khalilov et al, 2019) is isotypic with that of the title salt.…”

Section: Contactmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-chlorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide

et al. 2019

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The title salt, C16H15ClN3S+·Br−, is isotypic with (E)-3-[(4-fluorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide [Khalilov et al. (2019). Acta Cryst. E75, 662–666]. In the cation of the title salt, the atoms of the phenyl ring attached to the central thiazolidine ring and the atom joining the thiazolidine ring to the benzene ring are disordered over two sets of sites with occupancies of 0.570 (3) and 0.430 (3). The major and minor components of the disordered thiazolidine ring adopt slightly distorted envelope conformations, with the C atom bearing the phenyl ring as the flap atom. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N—H...Br hydrogen bonds, which are further connected by weak C—H...Br contacts into chains parallel to the a axis. Furthermore, not existing in the earlier report of (E)-3-[(4-fluorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide, C—H...π interactions and π–π stacking interactions [centroid-to-centroid distance = 3.897 (2) Å] between the major components of the disordered phenyl ring contribute to the stabilization of the molecular packing. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions for the crystal packing are from H...H (30.5%), Br...H/H...Br (21.2%), C...H/H...C (19.2%), Cl...H/H...Cl (13.0%) and S...H/H...S (5.0%) interactions.

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“…A search of the Cambridge Structural Database (CSD, Version 5.40, February 2019; Groom et al, 2016) for 2-thiazolidiniminium compounds gave ten hits, viz. MOJGUQ (Duruskari et al, 2019a), XOWXAL (Duruskari et al, 2019b), BOBWIB (Khalilov et al, 2019), UDELUN (Akkurt et al, 2018a), WILBIC (Marthi et al, 1994), WILBOI (Marthi et al, 1994), WILBOI01 (Marthi et al, 1994), YITCEJ (Martem'yanova et al, 1993a), YITCAF (Martem'yanova et al, 1993b) and YOPLUK (Marthi et al, 1995).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-3-(benzylideneamino)-5-phenylthiazolidin-2-iminium bromide

et al. 2020

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The central thiazolidine ring of the title salt, C16H16N3S+·Br−, adopts an envelope conformation, with the C atom bearing the phenyl ring as the flap atom. In the crystal, the cations and anions are linked by N—H...Br hydrogen bonds, forming chains parallel to the b-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (46.4%), C...H/H...C (18.6%) and H...Br/Br...H (17.5%) interactions.

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Structure of 2-amino-5-methylthiazoline and its N-methyl derivatives

Cited by 7 publications

References 1 publication

Crystal structure and Hirshfeld surface analysis of (E)-5-phenyl-3-[(pyridin-4-ylmethylidene)amino]thiazolidin-2-iminium bromide monohydrate

Crystal structure and Hirshfeld surface analysis of (E)-5-phenyl-3-[(pyridin-4-ylmethylidene)amino]thiazolidin-2-iminium bromide monohydrate

Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-chlorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide

Crystal structure and Hirshfeld surface analysis of (E)-3-(benzylideneamino)-5-phenylthiazolidin-2-iminium bromide

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