{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,12]],"date-time":"2026-02-12T13:39:57Z","timestamp":1770903597297,"version":"3.50.1"},"reference-count":50,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2021,8,10]],"date-time":"2021-08-10T00:00:00Z","timestamp":1628553600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["20-03-00119"],"award-info":[{"award-number":["20-03-00119"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Experimental and theoretical conformational analysis of N-methyl-N-[2-(diphenylphosphoryl)ethyl]diphenylphosphorylacetamide, N-butyl-N-[2-(diphenylphosphoryl)ethyl]diphenylphosphorylacetamide, and N-octyl-N-[2-(diphenylphosphoryl)ethyl]diphenylphosphorylacetamide was carried out by the methods of dipole moments, IR spectroscopy, and Density Functional Theory (DFT) B3PW91\/6-311++G(df,p) calculations. In solution, these N,N-dialkyl substituted bisphosphorylated acetamides exist as a conformational equilibrium of several forms divided into two groups\u2014with Z- or E-configuration of the carbonyl group and alkyl substituent, and syn or anti arrangement of the phosphoryl-containing fragments relative to the amide plane. The substituents at the phosphorus atoms have eclipsed cis- or staggered gauche-orientation relative to the P=O groups, and cis orientation of the substituents is due to the presence of intramolecular H-contacts P=O...H\u2212Cphenyl or p,\u03c0 conjugation between the phosphoryl group and the phenyl ring. Preferred conformers of acetamides molecules are additionally stabilized by various intramolecular hydrogen contacts with the participation of oxygen atoms of the P=O or C=O groups and hydrogen atoms of the methylene and ethylene bridges, alkyl substituents, and phenyl rings. However, steric factors, such as a flat amide fragment, the bulky phenyl groups, and the configuration of alkyl bridges, make a significant contribution to the realization of preferred conformers.<\/jats:p>","DOI":"10.3390\/molecules26164832","type":"journal-article","created":{"date-parts":[[2021,8,10]],"date-time":"2021-08-10T08:57:14Z","timestamp":1628585834000},"page":"4832","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Conformational Analysis of N-Alkyl-N-[2-(diphenylphosphoryl)ethyl]amides of Diphenylphosphorylacetic Acid: Dipole Moments, IR Spectroscopy, DFT Study"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6736-0698","authenticated-orcid":false,"given":"Anastasiia","family":"Kuznetsova","sequence":"first","affiliation":[{"name":"Department of Physical Chemistry, A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kremlevskaya 18, 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0073-3672","authenticated-orcid":false,"given":"Denis","family":"Chachkov","sequence":"additional","affiliation":[{"name":"Kazan Department of Joint Supercomputer Center of Russian Academy of Sciences, Branch of Federal Scientific Center \u201cScientific Research Institute for System Analysis of the RAS\u201d, Lobachevskogo 2\/31, 420111 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oleg","family":"Artyushin","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova 28, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Natalia","family":"Bondarenko","sequence":"additional","affiliation":[{"name":"Institute of Chemical Reagents and High Purity Chemical Substances of NRC \u201cKurchatov Institute\u201d, Bogorodsky val 3, 107076 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8259-8143","authenticated-orcid":false,"given":"Yana","family":"Vereshchagina","sequence":"additional","affiliation":[{"name":"Department of Physical Chemistry, A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kremlevskaya 18, 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,8,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"905","DOI":"10.1134\/S0036023620060248","article-title":"Extraction Properties of Diphenyl{[N-(2-diphenylphosphinylethyl)-N-alkyl]carbamoylmethyl}phosphine Oxides in Nitric Acid Solutions","volume":"65","author":"Turanov","year":"2020","journal-title":"Russ. J. Inorg. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1080\/07366299.2019.1592923","article-title":"Extraction of lanthanides(III) from Perchlorate Solutions with Carbamoyl- and Phosphorylmethoxymethylphosphine Oxides and Tetrabutyldiglycolamide","volume":"37","author":"Turanov","year":"2019","journal-title":"Solvent Extr. 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