FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2004572904> ?p ?o ?g. }

• W2004572904 endingPage "15843" @default.
• W2004572904 startingPage "15833" @default.
• W2004572904 abstract "While there is extensive information on 1,8-di(amino)naphthalene (i.e., the parent compound of the proton sponge series), the corresponding phosphorus compound has not been described. A high-yield synthesis of 1,8-di(phosphinyl)naphthalene (9) and the 1-naphthylphosphine reference compound (4) is now reported. Thermal decomposition of 9 leads to intramolecular dehydrogenative P-P coupling to afford 1,2-dihydro-1,2-diphosphaacenaphthene (10). Protonation of 9 and 4 with CF(3)SO(3)H gives quantitative yields of the monophosphonium salts 11 and 5, respectively. With excess acid and traces of moisture, the hydronium salt [C(10)H(6)(PH(2))(PH(3))](+)[H(3)O](+)2[CF(3)SO(3)](-) (13) is obtained. The structures of 9, 11, and 13 have been determined. Molecules of 9 have a planar naphthalene skeleton, C(10)H(6)P(2), with the two -PH(2) groups in a transoid conformation. The molecules form loose dimers in the crystal, the individual chiral enantiomers of which are related by a center of inversion. In contrast to the situation for the amino analogue, and despite the proximity of the two -PH(2) functions, there is no intra- or intermolecular hydrogen bonding. Solutions of 9 (in CD(2)Cl(2)) show equivalent P-bound hydrogen atoms due to conformational fluctionality. By analysis of the ABCD(2)XX'D'(2)C'B'A' spin system, it was shown that, in 9, there are strong through-space pericouplings [(n)J(P(X)P(X)(')) = 221.6 Hz, (n)J(P(X)H(D)(')) = 31.7 Hz, (n)J(H(D)H(D)(')) = 3.9 Hz]. In the cations of 11, the C(10)H(6)P(2) skeleton is also planar (by C(s) symmetry), with the -PH(2) and -PH(3)(+) groups in a conformation which rules out any P-H...P hydrogen bonding. The hydronium cation and the two triflate anions in 13 are associated into an anionic network through extensive hydrogen bonding surrounding stacks of the phosphonium cations. In solution, the cations of 11 and 13 show separate (31)P resonances for the two phosphorus atoms with fully resolved (1)J(PH) couplings, which indicate that there is no intra- or intercationic proton exchange. By contrast, the NMR spectra of solutions of [C(10)H(6)(NH(2))(NH(3))](+)X(-) salts show proton scrambling equilibrating all five N-bound hydrogen atoms, and in the crystal, the conformations of the cations feature intramolecular N-H...N hydrogen bonding." @default.
• W2004572904 created "2016-06-24" @default.
• W2004572904 creator A5011986282 @default.
• W2004572904 creator A5036764619 @default.
• W2004572904 creator A5049821973 @default.
• W2004572904 creator A5055589217 @default.
• W2004572904 date "2004-11-10" @default.
• W2004572904 modified "2023-09-24" @default.
• W2004572904 title "Insignificance of P−H···P Hydrogen Bonding: Structural Chemistry of Neutral and Protonated 1,8-Di(phosphinyl)naphthalene" @default.
• W2004572904 cites W1485947457 @default.
• W2004572904 cites W1570269399 @default.
• W2004572904 cites W1964864448 @default.
• W2004572904 cites W1967297440 @default.
• W2004572904 cites W1972681997 @default.
• W2004572904 cites W1977511037 @default.
• W2004572904 cites W1981230441 @default.
• W2004572904 cites W1982168837 @default.
• W2004572904 cites W1989754857 @default.
• W2004572904 cites W1991193044 @default.
• W2004572904 cites W1997108578 @default.
• W2004572904 cites W1997109025 @default.
• W2004572904 cites W1999313605 @default.
• W2004572904 cites W1999480281 @default.
• W2004572904 cites W2000731013 @default.
• W2004572904 cites W2005336091 @default.
• W2004572904 cites W2006478868 @default.
• W2004572904 cites W2009366610 @default.
• W2004572904 cites W2010475296 @default.
• W2004572904 cites W2011166181 @default.
• W2004572904 cites W2012053568 @default.
• W2004572904 cites W2014577898 @default.
• W2004572904 cites W2015816735 @default.
• W2004572904 cites W2016312264 @default.
• W2004572904 cites W2019968863 @default.
• W2004572904 cites W2029695869 @default.
• W2004572904 cites W2031223229 @default.
• W2004572904 cites W2032960970 @default.
• W2004572904 cites W2038358153 @default.
• W2004572904 cites W2045806234 @default.
• W2004572904 cites W2051392666 @default.
• W2004572904 cites W2055312596 @default.
• W2004572904 cites W2059999574 @default.
• W2004572904 cites W2064110908 @default.
• W2004572904 cites W2065867563 @default.
• W2004572904 cites W2072803460 @default.
• W2004572904 cites W2074670806 @default.
• W2004572904 cites W2083585397 @default.
• W2004572904 cites W2086924033 @default.
• W2004572904 cites W2090115806 @default.
• W2004572904 cites W2095014300 @default.
• W2004572904 cites W2099668627 @default.
• W2004572904 cites W2122360840 @default.
• W2004572904 cites W2135328775 @default.
• W2004572904 cites W2138767089 @default.
• W2004572904 cites W2153692893 @default.
• W2004572904 cites W2326537031 @default.
• W2004572904 cites W2949447905 @default.
• W2004572904 cites W2949650469 @default.
• W2004572904 cites W2949949523 @default.
• W2004572904 cites W2951408343 @default.
• W2004572904 cites W2951695872 @default.
• W2004572904 cites W4235412118 @default.
• W2004572904 cites W4256340587 @default.
• W2004572904 doi "https://doi.org/10.1021/ja045460x" @default.
• W2004572904 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15571408" @default.
• W2004572904 hasPublicationYear "2004" @default.
• W2004572904 type Work @default.
• W2004572904 sameAs 2004572904 @default.
• W2004572904 citedByCount "71" @default.
• W2004572904 countsByYear W20045729042012 @default.
• W2004572904 countsByYear W20045729042013 @default.
• W2004572904 countsByYear W20045729042014 @default.
• W2004572904 countsByYear W20045729042015 @default.
• W2004572904 countsByYear W20045729042016 @default.
• W2004572904 countsByYear W20045729042017 @default.
• W2004572904 countsByYear W20045729042019 @default.
• W2004572904 countsByYear W20045729042020 @default.
• W2004572904 countsByYear W20045729042021 @default.
• W2004572904 countsByYear W20045729042022 @default.
• W2004572904 crossrefType "journal-article" @default.
• W2004572904 hasAuthorship W2004572904A5011986282 @default.
• W2004572904 hasAuthorship W2004572904A5036764619 @default.
• W2004572904 hasAuthorship W2004572904A5049821973 @default.
• W2004572904 hasAuthorship W2004572904A5055589217 @default.
• W2004572904 hasConcept C112887158 @default.
• W2004572904 hasConcept C115624301 @default.
• W2004572904 hasConcept C145148216 @default.
• W2004572904 hasConcept C155647269 @default.
• W2004572904 hasConcept C166950319 @default.
• W2004572904 hasConcept C178790620 @default.
• W2004572904 hasConcept C185592680 @default.
• W2004572904 hasConcept C2779255514 @default.
• W2004572904 hasConcept C30095370 @default.
• W2004572904 hasConcept C32909587 @default.
• W2004572904 hasConcept C71240020 @default.
• W2004572904 hasConcept C75079739 @default.
• W2004572904 hasConcept C8010536 @default.
• W2004572904 hasConceptScore W2004572904C112887158 @default.

• next