Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage

Mouhamadou Birame Diop; Gorgui Awa Seck; Modou Sarr; Libasse Diop; Allen G. Oliver

doi:doi:10.11648/j.ajhc.20200602.11

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Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage

Mouhamadou Birame Diop, Gorgui Awa Seck, Modou Sarr, Libasse Diop, Allen G. Oliver

Published in American Journal of Heterocyclic Chemistry (Volume 6, Issue 2)

Received: 11 July 2020 Accepted: 27 July 2020 Published: 25 August 2020

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Abstract

Two oxalate compounds [(C₄H₇N₂)₃][Sb(C₂O₄)₃] (1) and [(Et₃NH)][SnPhCl(C₂O₄)₂] (2), have been isolated and characterized by single-crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic system, space group P2₁/c with a=13.3944 (6) Å, b=11.3554 (5) Å, c=16.3314 (7) Å, β=107.206 (1), V=2372.82 (18) Å³ and Z=4. Compound 2 crystallizes in the monoclinic system, space group P2₁/n with a=8.6903 (4) Å, b=15.3844 (8) Å, c=20.3144 (10) Å, β=100.869 (2), V=2667.2 (2) Å³ and Z=4. The complex-anion [Sb(O₂CCO₂)₃]^3- of the compound 1 adopts a distorted pentagonal pyramidal arrangement with monochelating oxalates. The asymmetric unit of 1 consists of three 2-methyl-1H-imidazolium cations, C₄H₇N₂⁺, three oxalate anions, C₂O₄^2-, and one antimony (III) ion, Sb³⁺. From a supramolecular point of view, in 1 complex-anions are connected by cations through N-H•••(O,O) and N-H•••O hydrogen bonds involving the two oxalates of the basal plane into sheets which are then connected via the remaining oxalate and cations through N-H•••O hydrogen bonds to give rise to a three-dimensional structure. The complex-anion of 2 is comprised of a tin centre linked to a chlorine atom and a phenyl group, and cis-chelated by two oxalates in a distorted octahedral fashion. Each triethylammonium cation is connected to the complex-anion through bifurcated N-H•••(O,O) hydrogen bonds. These interactions lead to a discrete structure. A double Sn-C bond cleavage has occurred during the process of the formation of the compound 2. In both complounds 1 and 2, one cation exhibits some positional disorder.

Published in	American Journal of Heterocyclic Chemistry (Volume 6, Issue 2)
DOI	10.11648/j.ajhc.20200602.11
Page(s)	16-23
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2020. Published by Science Publishing Group

Keywords

Oxalate, Antimony (III), Tin(IV), 2-Methylimidazolium, Triethylammonium, Sn-C Cleavage, X-ray Crystal Crystallography

References

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Mouhamadou Birame Diop, Gorgui Awa Seck, Modou Sarr, Libasse Diop, Allen G. Oliver. (2020). Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage. American Journal of Heterocyclic Chemistry, 6(2), 16-23. https://doi.org/10.11648/j.ajhc.20200602.11

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Mouhamadou Birame Diop; Gorgui Awa Seck; Modou Sarr; Libasse Diop; Allen G. Oliver. Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage. Am. J. Heterocycl. Chem. 2020, 6(2), 16-23. doi: 10.11648/j.ajhc.20200602.11

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AMA Style

Mouhamadou Birame Diop, Gorgui Awa Seck, Modou Sarr, Libasse Diop, Allen G. Oliver. Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage. Am J Heterocycl Chem. 2020;6(2):16-23. doi: 10.11648/j.ajhc.20200602.11

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@article{10.11648/j.ajhc.20200602.11,
  author = {Mouhamadou Birame Diop and Gorgui Awa Seck and Modou Sarr and Libasse Diop and Allen G. Oliver},
  title = {Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {6},
  number = {2},
  pages = {16-23},
  doi = {10.11648/j.ajhc.20200602.11},
  url = {https://doi.org/10.11648/j.ajhc.20200602.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20200602.11},
  abstract = {Two oxalate compounds [(C4H7N2)3][Sb(C2O4)3] (1) and [(Et3NH)][SnPhCl(C2O4)2] (2), have been isolated and characterized by single-crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic system, space group P21/c with a=13.3944 (6) Å, b=11.3554 (5) Å, c=16.3314 (7) Å, β=107.206 (1), V=2372.82 (18) Å3 and Z=4. Compound 2 crystallizes in the monoclinic system, space group P21/n with a=8.6903 (4) Å, b=15.3844 (8) Å, c=20.3144 (10) Å, β=100.869 (2), V=2667.2 (2) Å3 and Z=4. The complex-anion [Sb(O2CCO2)3]3- of the compound 1 adopts a distorted pentagonal pyramidal arrangement with monochelating oxalates. The asymmetric unit of 1 consists of three 2-methyl-1H-imidazolium cations, C4H7N2+, three oxalate anions, C2O42-, and one antimony (III) ion, Sb3+. From a supramolecular point of view, in 1 complex-anions are connected by cations through N-H•••(O,O) and N-H•••O hydrogen bonds involving the two oxalates of the basal plane into sheets which are then connected via the remaining oxalate and cations through N-H•••O hydrogen bonds to give rise to a three-dimensional structure. The complex-anion of 2 is comprised of a tin centre linked to a chlorine atom and a phenyl group, and cis-chelated by two oxalates in a distorted octahedral fashion. Each triethylammonium cation is connected to the complex-anion through bifurcated N-H•••(O,O) hydrogen bonds. These interactions lead to a discrete structure. A double Sn-C bond cleavage has occurred during the process of the formation of the compound 2. In both complounds 1 and 2, one cation exhibits some positional disorder.},
 year = {2020}
}

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TY  - JOUR
T1  - Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage
AU  - Mouhamadou Birame Diop
AU  - Gorgui Awa Seck
AU  - Modou Sarr
AU  - Libasse Diop
AU  - Allen G. Oliver
Y1  - 2020/08/25
PY  - 2020
N1  - https://doi.org/10.11648/j.ajhc.20200602.11
DO  - 10.11648/j.ajhc.20200602.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 16
EP  - 23
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20200602.11
AB  - Two oxalate compounds [(C4H7N2)3][Sb(C2O4)3] (1) and [(Et3NH)][SnPhCl(C2O4)2] (2), have been isolated and characterized by single-crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic system, space group P21/c with a=13.3944 (6) Å, b=11.3554 (5) Å, c=16.3314 (7) Å, β=107.206 (1), V=2372.82 (18) Å3 and Z=4. Compound 2 crystallizes in the monoclinic system, space group P21/n with a=8.6903 (4) Å, b=15.3844 (8) Å, c=20.3144 (10) Å, β=100.869 (2), V=2667.2 (2) Å3 and Z=4. The complex-anion [Sb(O2CCO2)3]3- of the compound 1 adopts a distorted pentagonal pyramidal arrangement with monochelating oxalates. The asymmetric unit of 1 consists of three 2-methyl-1H-imidazolium cations, C4H7N2+, three oxalate anions, C2O42-, and one antimony (III) ion, Sb3+. From a supramolecular point of view, in 1 complex-anions are connected by cations through N-H•••(O,O) and N-H•••O hydrogen bonds involving the two oxalates of the basal plane into sheets which are then connected via the remaining oxalate and cations through N-H•••O hydrogen bonds to give rise to a three-dimensional structure. The complex-anion of 2 is comprised of a tin centre linked to a chlorine atom and a phenyl group, and cis-chelated by two oxalates in a distorted octahedral fashion. Each triethylammonium cation is connected to the complex-anion through bifurcated N-H•••(O,O) hydrogen bonds. These interactions lead to a discrete structure. A double Sn-C bond cleavage has occurred during the process of the formation of the compound 2. In both complounds 1 and 2, one cation exhibits some positional disorder.
VL  - 6
IS  - 2
ER  -

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Author Information

Mouhamadou Birame Diop

Inorganic and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Gorgui Awa Seck

Inorganic and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Modou Sarr

Inorganic and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Libasse Diop

Inorganic and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Allen G. Oliver

Department of Chemistry and Biochemistry, University of Notre Dame, Nieuwland, Science Hall, Notre Dame, USA

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Mouhamadou Birame Diop, Gorgui Awa Seck, Modou Sarr, Libasse Diop, Allen G. Oliver. (2020). Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage. American Journal of Heterocyclic Chemistry, 6(2), 16-23. https://doi.org/10.11648/j.ajhc.20200602.11

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Mouhamadou Birame Diop; Gorgui Awa Seck; Modou Sarr; Libasse Diop; Allen G. Oliver. Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage. Am. J. Heterocycl. Chem. 2020, 6(2), 16-23. doi: 10.11648/j.ajhc.20200602.11

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Mouhamadou Birame Diop, Gorgui Awa Seck, Modou Sarr, Libasse Diop, Allen G. Oliver. Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage. Am J Heterocycl Chem. 2020;6(2):16-23. doi: 10.11648/j.ajhc.20200602.11

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@article{10.11648/j.ajhc.20200602.11,
  author = {Mouhamadou Birame Diop and Gorgui Awa Seck and Modou Sarr and Libasse Diop and Allen G. Oliver},
  title = {Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {6},
  number = {2},
  pages = {16-23},
  doi = {10.11648/j.ajhc.20200602.11},
  url = {https://doi.org/10.11648/j.ajhc.20200602.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20200602.11},
  abstract = {Two oxalate compounds [(C4H7N2)3][Sb(C2O4)3] (1) and [(Et3NH)][SnPhCl(C2O4)2] (2), have been isolated and characterized by single-crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic system, space group P21/c with a=13.3944 (6) Å, b=11.3554 (5) Å, c=16.3314 (7) Å, β=107.206 (1), V=2372.82 (18) Å3 and Z=4. Compound 2 crystallizes in the monoclinic system, space group P21/n with a=8.6903 (4) Å, b=15.3844 (8) Å, c=20.3144 (10) Å, β=100.869 (2), V=2667.2 (2) Å3 and Z=4. The complex-anion [Sb(O2CCO2)3]3- of the compound 1 adopts a distorted pentagonal pyramidal arrangement with monochelating oxalates. The asymmetric unit of 1 consists of three 2-methyl-1H-imidazolium cations, C4H7N2+, three oxalate anions, C2O42-, and one antimony (III) ion, Sb3+. From a supramolecular point of view, in 1 complex-anions are connected by cations through N-H•••(O,O) and N-H•••O hydrogen bonds involving the two oxalates of the basal plane into sheets which are then connected via the remaining oxalate and cations through N-H•••O hydrogen bonds to give rise to a three-dimensional structure. The complex-anion of 2 is comprised of a tin centre linked to a chlorine atom and a phenyl group, and cis-chelated by two oxalates in a distorted octahedral fashion. Each triethylammonium cation is connected to the complex-anion through bifurcated N-H•••(O,O) hydrogen bonds. These interactions lead to a discrete structure. A double Sn-C bond cleavage has occurred during the process of the formation of the compound 2. In both complounds 1 and 2, one cation exhibits some positional disorder.},
 year = {2020}
}

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TY  - JOUR
T1  - Co-crystallization of Oxalate Salts of Monoprotonated Amines with a Double Sn-Ph Bond Cleavage
AU  - Mouhamadou Birame Diop
AU  - Gorgui Awa Seck
AU  - Modou Sarr
AU  - Libasse Diop
AU  - Allen G. Oliver
Y1  - 2020/08/25
PY  - 2020
N1  - https://doi.org/10.11648/j.ajhc.20200602.11
DO  - 10.11648/j.ajhc.20200602.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 16
EP  - 23
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20200602.11
AB  - Two oxalate compounds [(C4H7N2)3][Sb(C2O4)3] (1) and [(Et3NH)][SnPhCl(C2O4)2] (2), have been isolated and characterized by single-crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic system, space group P21/c with a=13.3944 (6) Å, b=11.3554 (5) Å, c=16.3314 (7) Å, β=107.206 (1), V=2372.82 (18) Å3 and Z=4. Compound 2 crystallizes in the monoclinic system, space group P21/n with a=8.6903 (4) Å, b=15.3844 (8) Å, c=20.3144 (10) Å, β=100.869 (2), V=2667.2 (2) Å3 and Z=4. The complex-anion [Sb(O2CCO2)3]3- of the compound 1 adopts a distorted pentagonal pyramidal arrangement with monochelating oxalates. The asymmetric unit of 1 consists of three 2-methyl-1H-imidazolium cations, C4H7N2+, three oxalate anions, C2O42-, and one antimony (III) ion, Sb3+. From a supramolecular point of view, in 1 complex-anions are connected by cations through N-H•••(O,O) and N-H•••O hydrogen bonds involving the two oxalates of the basal plane into sheets which are then connected via the remaining oxalate and cations through N-H•••O hydrogen bonds to give rise to a three-dimensional structure. The complex-anion of 2 is comprised of a tin centre linked to a chlorine atom and a phenyl group, and cis-chelated by two oxalates in a distorted octahedral fashion. Each triethylammonium cation is connected to the complex-anion through bifurcated N-H•••(O,O) hydrogen bonds. These interactions lead to a discrete structure. A double Sn-C bond cleavage has occurred during the process of the formation of the compound 2. In both complounds 1 and 2, one cation exhibits some positional disorder.
VL  - 6
IS  - 2
ER  -

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