{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,6,6]],"date-time":"2024-06-06T09:20:14Z","timestamp":1717665614377},"reference-count":66,"publisher":"Wiley","issue":"20","license":[{"start":{"date-parts":[[2014,6,12]],"date-time":"2014-06-12T00:00:00Z","timestamp":1402531200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["NSF CHE-105-7466"],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J Comput Chem"],"published-print":{"date-parts":[[2014,7,30]]},"abstract":"We use comparative natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) methods to analyze the proximal bay\u2010type H\u00b7\u00b7\u00b7H interactions in cis\u20102\u2010butene and related species, which lead to controversial interpretation as attractive \u201cH\uf8ffH bonding\u201d in the QTAIM framework. We address the challenging questions concerning well established structural, conformational, and vibrational properties of such species that appear to be sharply at odds with the QTAIM interpretation. In contrast to the purported \u201cH\uf8ffH bonding\u201d of QTAIM theory, NBO\u2010based evaluation of steric (donor\u2013donor) and hyperconjugative (donor\u2013acceptor) interactions unambiguously portrays such H\u00b7\u00b7\u00b7H contacts as dominated by steric clashes that are only partially softened by weak secondary hyperconjugative interactions, contributing negligibly (b<\/jats:italic>HH<\/jats:sub>\u2009<\u20090.01) to H\u00b7\u00b7\u00b7H bond order. Additional details of NBO\u2010based versus QTAIM\u2010based description are provided by natural bond critical point analysis of topological bond critical point properties, which further emphasizes the contrast between the problematic bay\u2010type H\u00b7\u00b7\u00b7H contacts and remaining noncontroversial (consensus) chemical bonds. NBO analysis is thereby shown to be fully consistent with the traditional physical organic concept of repulsive bay\u2010type H\u00b7\u00b7\u00b7H contacts, including the corollary array of structural, conformational, and vibrational properties. \u00a9 2014 Wiley Periodicals, Inc.<\/jats:p>","DOI":"10.1002\/jcc.23654","type":"journal-article","created":{"date-parts":[[2014,6,12]],"date-time":"2014-06-12T09:00:24Z","timestamp":1402563624000},"page":"1499-1508","source":"Crossref","is-referenced-by-count":58,"title":["Bay\u2010type H\u00b7\u00b7\u00b7H \u201cbonding\u201d in cis\u20102\u2010butene and related species: QTAIM versus NBO description"],"prefix":"10.1002","volume":"35","author":[{"given":"Frank","family":"Weinhold","sequence":"first","affiliation":[{"name":"Department of Chemistry Theoretical Chemistry Institute, University of Wisconsin Madison Wisconsin 53706"}]},{"given":"Paul von Ragu\u00e9","family":"Schleyer","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Georgia Athens Georgia 30602"}]},{"given":"William Chadwick","family":"McKee","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Georgia Athens Georgia 30602"}]}],"member":"311","published-online":{"date-parts":[[2014,6,12]]},"reference":[{"key":"e_1_2_8_1_1","volume-title":"Atoms in Molecules: A Quantum Theory","author":"Bader R. 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