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Crystal and Molecular Structures of Four Organic Acid–Base Adducts from Hexamethylenetetramine, N,N,N,N-Tetramethylethylenediamine, and Organic Acids

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Abstract

The preparation, X-ray crystal structure, Fourier Transform infrared (FTIR) spectroscopy, and elemental analysis of the four compounds based on hexamethylenetetramine, and N, N, N, N-tetramethylethylenediamine are reported. XRD and FTIR analysis indicated that the compound 1 is a cocrystal, while 2-4 are organic salts. The compound 1 crystallizes in the triclinic, space group P-1, with a = 7.9280(6) Å, b = 11.1452(9) Å, c = 18.2226(16) Å, α = 80.9580(10)°, β = 86.285(2)°, γ = 70.1740(10)°,V = 1495.8(2) Å3, Z = 2. The compound 2 crystallizes in the monoclinic, space group P2(1)/c, with a = 11.4207(9) Å, b = 10.1095(6) Å, c = 14.9048(12) Å, α = 90°, β = 96.2950(10)°, γ = 90°, V = 1710.5(2) Å3, Z = 4. The compound 3 crystallizes in the Triclinic, space group P-1, with a = 7.6542(6) Å, b = 12.2296(11) Å, c = 13.9565(12) Å, α = 67.6900(10)°, β = 85.571(2)°, γ = 71.8270(10)°, V = 1147.09(17) Å3, Z = 2. The compound 4 crystallizes in the monoclinic, space group P2(1)/c, with a = 6.9377(5) Å, b = 12.0824(9) Å, c = 12.1639(11) Å, α = 90°, β = 94.6840(10)°, γ = 90°, V = 1016.22(14) Å3, Z = 2. In this work, the hexamethylenetetramine at 1–2 formed two, three and four classical hydrogen bonds, respectively. Each NH+ at the diprotonated N, N, N, N-tetramethylethylenediamine generated one or two hydrogen bonds. In addition to the classical hydrogen bonds, the auxiliary expanding interactions as CH–O, CH2–O, CH3–O, CH2···Cπ, CH2-π and CH3-π also play important roles in the structure extension. In conclusion, we have shown that 3D structures can be constructed by the collective non-covalent interactions.

Graphical Abstract

In the four prepared supramolecular assemblies there are plenty of weak nonbonding interactions such as directional hydrogen bonds of O–H···N, N–H···O, O–H···O, N–H···S, intra- and interchain CH–O, CH2···O, CH3–O, CH2···Cπ, CH2-π and CH3-π interactions. Due to these collective weak interactions, all the compounds displayed the 3D framework structures.

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Acknowledgments

This research was supported by Zhejiang Provincial Natural Science Foundation of China under Grant No. LY14B010006, the Education Office Foundation of Zhejiang Province under Grant No. Y201017321, the National Training Programs of Innovation and Entrepreneurship of China for Undergraduates under Grant No. 201410341022, the Open Foundation of Key Laboratory of Chemical Utilization of Forestry Biomass of Zhejiang Province, Zhejiang A & F University under Grant No. 2015CUFB02, Zhejiang Provincial Municipal Science and Technology Project under Grant No. 2014C32040, Zhejiang Provincial Natural Science Foundation of China under Grant No. LY14E030016, Preresearch Project of Research Center of Biomass Resource Utilization, Zhejiang A & F University under Grant No. 2013SWZ03-2, and the Open Fund of Zhejiang Provincial Top Key Discipline of Forestry Engineering under Grant No. 2014LYGCZ017.

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Authors and Affiliations

  1. Jiyang College ZheJiang A & F University, Zhu’Ji, 311800, People’s Republic of China

    Ying Zhao, Shouwen **, Zhaohui Tao, Yi Lin & Lanqing Wang

  2. Key Laboratory of Chemical Utilization of Forestry Biomass of Zhejiang Province Zhejiang A & F University, Lin’an, 311300, Zhejiang Province, China

    Ying Zhao, Shouwen **, Zhaohui Tao, Yi Lin, Lanqing Wang, Jianzhong Guo & Ming Guo

  3. Department of Chemistry, Liaocheng University, Liaocheng, 252059, People’s Republic of China

    Daqi Wang

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  1. Ying Zhao
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Correspondence to Shouwen **.

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Zhao, Y., **, S., Tao, Z. et al. Crystal and Molecular Structures of Four Organic Acid–Base Adducts from Hexamethylenetetramine, N,N,N,N-Tetramethylethylenediamine, and Organic Acids. J Chem Crystallogr 46, 188–202 (2016). https://doi.org/10.1007/s10870-016-0647-x

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