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.

Základní údaje

Originální název

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

Autoři

POURAYOUBI, Mehrdad (364 Írán), Mozhgan ABRISHAMI (364 Írán), Václav EIGNER (203 Česká republika), Marek NEČAS (203 Česká republika, garant, domácí), Michal DUŠEK (203 Česká republika) a Mahmoud DELAVAR (364 Írán)

Vydání

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

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10402 Inorganic and nuclear chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 0.326

Kód RIV

RIV/00216224:14740/14:00079169

Organizační jednotka

Středoevropský technologický institut

DOI

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

UT WoS

000345959700013

Klíčová slova anglicky

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

Štítky

kontrola MP, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 13. 3. 2018 10:25, doc. Mgr. Marek Nečas, Ph.D.

Anotace

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 a 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, roč. 70, č. 12, s. 1147-1152. ISSN 0108-2701. Dostupné z: 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 a 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, roč.~70, č.~12, s.~1147-1152. ISSN~0108-2701. Dostupné z: https://dx.doi.org/10.1107/S2053229614022608.

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