Extensive analysis of N-H center dot center dot center dot O hydrogen bonding in four classes of phosphorus compounds: a combined experimental and database study

HAMZEHEE, Farahnaz, Mehrdad POURAYOUBI, Marek NEČAS and Duane CHOQUESILLO-LAZARTE. Extensive analysis of N-H center dot center dot center dot O hydrogen bonding in four classes of phosphorus compounds: a combined experimental and database study. ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY. CHESTER: INT UNION CRYSTALLOGRAPHY, 2017, vol. 73, March, p. 287-297, 31 pp. ISSN 2053-2296. Available from: https://dx.doi.org/10.1107/S2053229617001516.

Basic information

• Original name: Extensive analysis of N-H center dot center dot center dot O hydrogen bonding in four classes of phosphorus compounds: a combined experimental and database study
• Authors: HAMZEHEE, Farahnaz (364 Islamic Republic of Iran), Mehrdad POURAYOUBI (364 Islamic Republic of Iran), Marek NEČAS (203 Czech Republic, guarantor, belonging to the institution) and Duane CHOQUESILLO-LAZARTE (724 Spain).
• Edition: ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, CHESTER, INT UNION CRYSTALLOGRAPHY, 2017, 2053-2296.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10402 Inorganic and nuclear chemistry
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 8.678
• RIV identification code: RIV/00216224:14310/17:00100454
• Organization unit: Faculty of Science
• Doi: http://dx.doi.org/10.1107/S2053229617001516
• UT WoS: 000395789800023
• Keywords in English: phosphorus compound; crystal structure; hydrogen bonding; Cambridge Structural Database; positive/negative charge-assisted N-H center dot center dot center dot O hydrogen bonds
• Tags: CF SAXS, NZ, rivok
• Tags: International impact, Reviewed

Abstract

The N-H center dot center dot center dot O hydrogen bond is the characteristic interaction in the crystal structures of N-benzyl-P-phenyl-N'-(p-tolyl) phosphonic diamide, C20H21N2OP or (C6H5)P(O)(NHCH2C6H5)(NHC6H4-p-CH3), (I), diphenylphosphinic 1-methylpropylamide, C16H20NOP or (C6H5)(2)P(O)[NHCH(CH3)(C2H5)], (II), (S)-1-phenylethylammonium N-[(S)-1-phenylethyl] phenylphosphonamidate, C8H12N+center dot-C14H15NO2P- or [S-(C6H5)CH(CH3)NH3][(C6H5)P(O){S-NHCH(CH3)(C6H5)}(O)], (III), and (4-methylbenzyl) ammonium diphenylphosphinate, C8H12N+center dot-C12H10O2P- or [4-CH3-C6H4CH2NH3][(C6H5)(2)P(O)(O)], (IV). This article focuses on the N-H center dot center dot center dot O hydrogen bonds by considering the structures of (I), (II), (III) and (IV), and reviewing their analogous compounds, including 43 (C)P(O)(N)(2), 102 (C)(2)P(O)(N), 31 (C) P(O)(N)(O) and 96 (C)(2)P(O)(O) structures, deposited in the Cambridge Structural Database (CSD). For the structures with a (C) P(O)(N) 2 segment, only neutral hydrogen bonds were found in the CSD. The other three classes of compounds included both neutral and 'charge-assisted' hydrogen bonds, and the (C) 2P(O)(O) structures were particularly noticeable for a high number of cation-anion compounds. The overall tendencies of N center dot center dot center dot O distances in neutral and cation-anion compounds were compared. The N-H center dot center dot center dot O hydrogen-bond angles were also analyzed for the four classes of phosphorus compounds.

Links

• LM2015043, research and development project: Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR