Competitor hydrogen-bond acceptors in the SP(NH)3-based
structures: Comparison of structural features –
Computational/database and experimental

J 2022

Competitor hydrogen-bond acceptors in the SP(NH)3-based structures: Comparison of structural features – Computational/database and experimental

KHORRAMAKI, Maliheh, Mohammad ABAD, Vahidreza DARUGAR, Mehrdad POURAYOUBI, Mohammad VAKILI et. al.

Basic information

Original name

Competitor hydrogen-bond acceptors in the SP(NH)3-based structures: Comparison of structural features – Computational/database and experimental

Authors

KHORRAMAKI, Maliheh, Mohammad ABAD, Vahidreza DARUGAR, Mehrdad POURAYOUBI (guarantor), Mohammad VAKILI, Marek NEČAS (203 Czech Republic, belonging to the institution), Duane CHOQUESILLO-LAZARTE, Pavel V. ANDREEV and Ekaterina S. SHCHEGRAVINA

Edition

Polyhedron, Elsevier, 2022, 0277-5387

Other information

Language

English

Type of outcome

Article in a journal

Field of Study

10400 1.4 Chemical sciences

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

is not subject to a state or trade secret

References:

URL

Impact factor

Impact factor: 2.600

RIV identification code

RIV/00216224:14310/22:00128142

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.poly.2022.116157

UT WoS

000877346700002

Keywords in English

Phosphorothioic triamide; Mercury(II) complex; Hirshfeld surface analysis; DFT; NBO

Abstract

V originále

The phosphorothioic triamides (4-Cl-C6H4CH2NH)3P(S) (I) and (4-CH3-C6H4CH2NH)3P(S) (II) were synthesized to study their coordination behaviors towards Hg(II) cation. The resulting complexes, [(4-Cl-C6H4CH2NH)3P(S)]2Hg2Cl4 (III) and [(4-CH3-C6H4CH2NH)3P(S)]2Hg2Cl4 (IV), are the first examples of mercury complexes with SP(NHR)3 ligands characterized by X-ray crystallography. The presence of NH/CH units and some potential competitor acceptors with moderate/weak acceptor capabilities (sulfur, chlorine and π system) provides the opportunity to study the hydrogen bond elements of (I), (III) and (IV), structurally and of all four compounds theoretically. The strengths of inter- and intramolecular hydrogen bonds were assessed by quantum chemical calculations (Atoms In Molecules (AIM), and Natural Bond Orbital (NBO)), and the internal interactions were further examined by reduced density gradient (RDG) analysis. The differences/similarities of structures were addressed in the view point of geometry, conformations related to flexible substituted benzyl moieties, crowding in the structures and non-bonded contacts, stabilization of four-membered Hg2Cl2 rings and some topics related to solution nuclear magnetic resonance studies (chemical shifts and coupling constants). The similarity of structures investigated allowed for a precise assignment of vibrational frequencies. A survey of the Hg—Sdouble bondP segment in the Cambridge Structural Database shows that the Hg—S bond lengths in (III) and (IV) are among the smallest Hg—S bonds in the structures with the thiophosphoryl-holding ligands.

Links

90127, large research infrastructures

Name: CIISB II

Citovat

KHORRAMAKI, Maliheh, Mohammad ABAD, Vahidreza DARUGAR, Mehrdad POURAYOUBI, Mohammad VAKILI, Marek NEČAS, Duane CHOQUESILLO-LAZARTE, Pavel V. ANDREEV and Ekaterina S. SHCHEGRAVINA. Competitor hydrogen-bond acceptors in the SP(NH)3-based structures: Comparison of structural features – Computational/database and experimental. Polyhedron. Elsevier, 2022, vol. 228, December, p. 1-15. ISSN 0277-5387. Available from: https://dx.doi.org/10.1016/j.poly.2022.116157.

@article{2247910,
   author = {Khorramaki, Maliheh and Abad, Mohammad and Darugar, Vahidreza and Pourayoubi, Mehrdad and Vakili, Mohammad and Nečas, Marek and ChoquesilloandLazarte, Duane and Andreev, Pavel V. and Shchegravina, Ekaterina S.},
   article_number = {December},
   doi = {http://dx.doi.org/10.1016/j.poly.2022.116157},
   keywords = {Phosphorothioic triamide; Mercury(II) complex; Hirshfeld surface analysis; DFT; NBO},
   language = {eng},
   issn = {0277-5387},
   journal = {Polyhedron},
   title = {Competitor hydrogen-bond acceptors in the SP(NH)3-based structures: Comparison of structural features – Computational/database and experimental},
   url = {https://www.sciencedirect.com/science/article/pii/S0277538722005095},
   volume = {228},
   year = {2022}
}

TY  - JOUR
ID  - 2247910
AU  - Khorramaki, Maliheh - Abad, Mohammad - Darugar, Vahidreza - Pourayoubi, Mehrdad - Vakili, Mohammad - Nečas, Marek - Choquesillo-Lazarte, Duane - Andreev, Pavel V. - Shchegravina, Ekaterina S.
PY  - 2022
TI  - Competitor hydrogen-bond acceptors in the SP(NH)3-based structures: Comparison of structural features – Computational/database and experimental
JF  - Polyhedron
VL  - 228
IS  - December
SP  - 1-15
EP  - 1-15
PB  - Elsevier
SN  - 02775387
KW  - Phosphorothioic triamide
KW  - Mercury(II) complex
KW  - Hirshfeld surface analysis
KW  - DFT
KW  - NBO
UR  - https://www.sciencedirect.com/science/article/pii/S0277538722005095
N2  - The phosphorothioic triamides (4-Cl-C6H4CH2NH)3P(S) (I) and (4-CH3-C6H4CH2NH)3P(S) (II) were synthesized to study their coordination behaviors towards Hg(II) cation. The resulting complexes, [(4-Cl-C6H4CH2NH)3P(S)]2Hg2Cl4 (III) and [(4-CH3-C6H4CH2NH)3P(S)]2Hg2Cl4 (IV), are the first examples of mercury complexes with SP(NHR)3 ligands characterized by X-ray crystallography. The presence of NH/CH units and some potential competitor acceptors with moderate/weak acceptor capabilities (sulfur, chlorine and π system) provides the opportunity to study the hydrogen bond elements of (I), (III) and (IV), structurally and of all four compounds theoretically. The strengths of inter- and intramolecular hydrogen bonds were assessed by quantum chemical calculations (Atoms In Molecules (AIM), and Natural Bond Orbital (NBO)), and the internal interactions were further examined by reduced density gradient (RDG) analysis. The differences/similarities of structures were addressed in the view point of geometry, conformations related to flexible substituted benzyl moieties, crowding in the structures and non-bonded contacts, stabilization of four-membered Hg2Cl2 rings and some topics related to solution nuclear magnetic resonance studies (chemical shifts and coupling constants). The similarity of structures investigated allowed for a precise assignment of vibrational frequencies. A survey of the Hg—Sdouble bondP segment in the Cambridge Structural Database shows that the Hg—S bond lengths in (III) and (IV) are among the smallest Hg—S bonds in the structures with the thiophosphoryl-holding ligands.
ER  -

KHORRAMAKI, Maliheh, Mohammad ABAD, Vahidreza DARUGAR, Mehrdad POURAYOUBI, Mohammad VAKILI, Marek NEČAS, Duane CHOQUESILLO-LAZARTE, Pavel V. ANDREEV and Ekaterina S. SHCHEGRAVINA. Competitor hydrogen-bond acceptors in the SP(NH)3-based structures: Comparison of structural features – Computational/database and experimental. \textit{Polyhedron}. Elsevier, 2022, vol.~228, December, p.~1-15. ISSN~0277-5387. Available from: https://dx.doi.org/10.1016/j.poly.2022.116157.

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