Two new thiophosphoramide structures: N,N ',N
''-tricyclohexylphosphorothioic triamide and O,O '-diethyl
(2-phenylhydrazin-1-yl)thiophosphonate

J 2014

Two new thiophosphoramide structures: N,N ',N ''-tricyclohexylphosphorothioic triamide and O,O '-diethyl (2-phenylhydrazin-1-yl)thiophosphonate

POURAYOUBI, Mehrdad, Mozhgan ABRISHAMI, Václav EIGNER, Marek NEČAS, Michal DUŠEK et. al.

Basic information

Original name

Two new thiophosphoramide structures: N,N ',N ''-tricyclohexylphosphorothioic triamide and O,O '-diethyl (2-phenylhydrazin-1-yl)thiophosphonate

Authors

POURAYOUBI, Mehrdad (364 Islamic Republic of Iran), Mozhgan ABRISHAMI (364 Islamic Republic of Iran), Václav EIGNER (203 Czech Republic), Marek NEČAS (203 Czech Republic, guarantor, belonging to the institution), Michal DUŠEK (203 Czech Republic) and Mahmoud DELAVAR (364 Islamic Republic of Iran)

Edition

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, HOBOKEN, WILEY-BLACKWELL, 2014, 0108-2701

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10402 Inorganic and nuclear chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 0.326

RIV identification code

RIV/00216224:14740/14:00079169

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1107/S2053229614022608

UT WoS

000345959700013

Keywords in English

crystal structure; thiophosphoramide; database analysis; P(S)[O](2)[N] skeleton; phosphorothioic triamide; P(S)[N](3) skeleton; N-H center dot center dot center dot S hydrogen bond; NMR experiment

Abstract

V originále

The compound N,N',N"-tricyclohexylphosphorothioic triamide, C18H36N3PS or P(S)[NHC6H11](3), (I), crystallizes in the space group Pnma with the molecule lying across a mirror plane; one N atom lies on the mirror plane, whereas the bond-angle sum at the other N atom has a deviation of some 8 degrees from the ideal value of 360 degrees for a planar configuration. The orientation of the atoms attached to this nonplanar N atom corresponds to an anti orientation of the corresponding lone electron pair (LEP) with respect to the P=S group. The P=S bond length of 1.9785 (6) angstrom is within the expected range for compounds with a P(S)[N](3) skeleton; however, it is in the region of the longest bond lengths found for analogous structures. This may be due to the involvement of the P=S group in N-H center dot center dot center dot S=P hydrogen bonds. In O,O'-diethyl (2-phenylhydrazin-1-yl)thiophosphonate, C10H17N2O2PS or P(S)[OC2H5](2)[NHNHC6H5], (II), the bond-angle sum at the N atom attached to the phenyl ring is 345.1 degrees, whereas, for the N atom bonded to the P atom, a practically planar environment is observed, with a bond-angle sum of 359.1 degrees. A Cambridge Structural Database [CSD; Allen (2002). Acta Cryst. B58, 380-388] analysis shows a shift of the maximum population of P=S bond lengths in compounds with a P(S)[O](2)[N] skeleton to the shorter bond lengths relative to compounds with a P(S)[N](3) skeleton. The influence of this difference on the collective tendencies of N center dot center dot center dot S distances in N-H center dot center dot center dot S hydrogen bonds for structures with P(S)[N](3) and P(S)[O](2)[N] segments were studied through a CSD analysis.

Citovat

POURAYOUBI, Mehrdad, Mozhgan ABRISHAMI, Václav EIGNER, Marek NEČAS, Michal DUŠEK and Mahmoud DELAVAR. Two new thiophosphoramide structures: N,N ',N ''-tricyclohexylphosphorothioic triamide and O,O '-diethyl (2-phenylhydrazin-1-yl)thiophosphonate. ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY. HOBOKEN: WILEY-BLACKWELL, 2014, vol. 70, No 12, p. 1147-1152. ISSN 0108-2701. Available from: https://dx.doi.org/10.1107/S2053229614022608.

@article{1227189,
   author = {Pourayoubi, Mehrdad and Abrishami, Mozhgan and Eigner, Václav and Nečas, Marek and Dušek, Michal and Delavar, Mahmoud},
   article_location = {HOBOKEN},
   article_number = {12},
   doi = {http://dx.doi.org/10.1107/S2053229614022608},
   keywords = {crystal structure; thiophosphoramide; database analysis; P(S)[O](2)[N] skeleton; phosphorothioic triamide; P(S)[N](3) skeleton; N-H center dot center dot center dot S hydrogen bond; NMR experiment},
   language = {eng},
   issn = {0108-2701},
   journal = {ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY},
   title = {Two new thiophosphoramide structures: N,N ',N ''-tricyclohexylphosphorothioic triamide and O,O '-diethyl (2-phenylhydrazin-1-yl)thiophosphonate},
   volume = {70},
   year = {2014}
}

TY  - JOUR
ID  - 1227189
AU  - Pourayoubi, Mehrdad - Abrishami, Mozhgan - Eigner, Václav - Nečas, Marek - Dušek, Michal - Delavar, Mahmoud
PY  - 2014
TI  - Two new thiophosphoramide structures: N,N ',N ''-tricyclohexylphosphorothioic triamide and O,O '-diethyl (2-phenylhydrazin-1-yl)thiophosphonate
JF  - ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
VL  - 70
IS  - 12
SP  - 1147-1152
EP  - 1147-1152
PB  - WILEY-BLACKWELL
SN  - 01082701
KW  - crystal structure
KW  - thiophosphoramide
KW  - database analysis
KW  - P(S)[O](2)[N] skeleton
KW  - phosphorothioic triamide
KW  - P(S)[N](3) skeleton
KW  - N-H center dot center dot center dot S hydrogen bond
KW  - NMR experiment
N2  - The compound N,N',N"-tricyclohexylphosphorothioic triamide, C18H36N3PS or P(S)[NHC6H11](3), (I), crystallizes in the space group Pnma with the molecule lying across a mirror plane; one N atom lies on the mirror plane, whereas the bond-angle sum at the other N atom has a deviation of some 8 degrees from the ideal value of 360 degrees for a planar configuration. The orientation of the atoms attached to this nonplanar N atom corresponds to an anti orientation of the corresponding lone electron pair (LEP) with respect to the P=S group. The P=S bond length of 1.9785 (6) angstrom is within the expected range for compounds with a P(S)[N](3) skeleton; however, it is in the region of the longest bond lengths found for analogous structures. This may be due to the involvement of the P=S group in N-H center dot center dot center dot S=P hydrogen bonds. In O,O'-diethyl (2-phenylhydrazin-1-yl)thiophosphonate, C10H17N2O2PS or P(S)[OC2H5](2)[NHNHC6H5], (II), the bond-angle sum at the N atom attached to the phenyl ring is 345.1 degrees, whereas, for the N atom bonded to the P atom, a practically planar environment is observed, with a bond-angle sum of 359.1 degrees. A Cambridge Structural Database [CSD; Allen (2002). Acta Cryst. B58, 380-388] analysis shows a shift of the maximum population of P=S bond lengths in compounds with a P(S)[O](2)[N] skeleton to the shorter bond lengths relative to compounds with a P(S)[N](3) skeleton. The influence of this difference on the collective tendencies of N center dot center dot center dot S distances in N-H center dot center dot center dot S hydrogen bonds for structures with P(S)[N](3) and P(S)[O](2)[N] segments were studied through a CSD analysis.
ER  -

POURAYOUBI, Mehrdad, Mozhgan ABRISHAMI, Václav EIGNER, Marek NEČAS, Michal DUŠEK and Mahmoud DELAVAR. Two new thiophosphoramide structures: N,N ',N ''-tricyclohexylphosphorothioic triamide and O,O '-diethyl (2-phenylhydrazin-1-yl)thiophosphonate. \textit{ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY}. HOBOKEN: WILEY-BLACKWELL, 2014, vol.~70, No~12, p.~1147-1152. ISSN~0108-2701. Available from: https://dx.doi.org/10.1107/S2053229614022608.

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