Synthesis and crystal structures of inclusion compounds of 2,2'-dithiosalicylic acid and triethylamine/tripropylamine
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TRUCTURE OF ORGANIC COMPOUNDS
Synthesis and Crystal Structures of Inclusion Compounds of 2,2'-Dithiosalicylic Acid and Triethylamine/Tripropylamine1 Y. X. Yang, H. Y. Li, and J. F. Wu Key Laboratory of Polymer Materials of Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, Gansu, China e-mail: [email protected] Received May 23, 2014
Abstract—Herein we reported two new inclusion compounds of 2,2'-dithiosalicylic acid (C14H10O4S2, DTSA) and triethylamine and tripropylamine, [C14H8O4S 22 − · [N+(C2H5)3]2 · H2O] (1) and [C14H10O4S2 · C14H8O4S 22 − · [N+(C3H7)3]2] (2). Compound 1: triclinic P1, a = 8.2159(2), b = 12.5724(3), c = 14.9203(3) Å, α = 97.0390(10), β = 101.4310(10)°, γ = 101.3370(10)°, V = 1460.06(6) Å3, Z = 2, R1 = 0.0526, wR2 = 0.1495; Compound 2: monoclinic P21/c, a = 20.5178(13), b = 15.3623(8), c = 15.5529(9) Å, β = 102.036(3)°, V = 4794.5(5) Å3, Z = 4, R1 = 0.0533, wR2 = 0.1252. In these two crystal structures, DTSA utilizes conventional O–H···O hydrogen bonds to link to generate varied host lattices, in which the central N atoms of the guest amine molecules accept the protons of DTSA to form the corresponding cations to act as the couterions to develop the stable crystal structures. Noticeably, except Van der Waals forces usually existing between the host and guest molecules, the central N atoms of the guests of the two compounds can construct strong N–H…O hydrogen bonds with the related host molecules, which further enforce the host-guest interactions to help form the final inclusion compounds. DOI: 10.1134/S1063774515070329
1. INTRODUCTION Inclusion compound, which has been studied since 1940 [1], is a kind of complicated system composed of intermolecular forces but normal covalent bonds. There are two types of inclusion compounds: molecular inclusion and crystal lattice inclusion. However, there mainly exist Van der Waals forces between the host and guest molecules in either inclusion compounds. Recently, our group has synthesized many urea/thiourea inclusion compounds with the guest template being the sphere-like tetraalkylammonium [2–5]. Meanwhile, we also used multidentate carboxyl/hydroxyl multicyclic host molecules to interact with the same guest template to prepare many novel inclusion compounds [6, 7]. Our results showed that the guest molecules mostly depend on Van der Waals forces to interact with the host molecules to form the stable structures in the inclusion compounds we have obtained. Based on the experimental foundation, we selected the same multidentate carboxyl/hydroxyl multicyclic host molecules, but substituted the guest template with the neutral trigonal pyramidal amine molecules to prepare the inclusion compounds to further explore the host-guest interactions in the related 1 The article is published in the original.
structures, which can help us understand the complicated forces and the crystal packing modes of the hostguest system. COOH S S
COOH
Scheme 1.
As a typical host molecule we appreciated, 2,2'dithiosa
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