{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T18:50:54Z","timestamp":1760986254892,"version":"build-2065373602"},"reference-count":90,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2023,12,28]],"date-time":"2023-12-28T00:00:00Z","timestamp":1703721600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2024,1,15]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Carbones (carbodiphosphoranes, bent allenes and chalcogen\u2010stabilized carbones) bear the same resonance contributor X<jats:sup>+<\/jats:sup>\u2212C<jats:sup>2\u2212<\/jats:sup>\u2212Y<jats:sup>+<\/jats:sup> (X<jats:sup>+<\/jats:sup>, Y<jats:sup>+<\/jats:sup>=PR<jats:sub>3<\/jats:sub><jats:sup>+<\/jats:sup>, CR<jats:sub>2<\/jats:sub><jats:sup>+<\/jats:sup>, SR<jats:sub>2<\/jats:sub><jats:sup>+<\/jats:sup>, SeR<jats:sub>2<\/jats:sub><jats:sup>+<\/jats:sup>, S<jats:sup>+<\/jats:sup>R<jats:sub>2<\/jats:sub>=NR) and exhibit unique bonding and donating properties at the central carbon atom. A classification is given on basis of both the geometry and the magnetic properties (<jats:sup>13<\/jats:sup>C chemical shift of the central carbon atom and the spatial magnetic properties, through\u2010space NMR shieldings (TS\u2005NMRSs), actually the anisotropy effect or the ring current effect of aromatic species). TS\u2005NMRS values have been calculated using the GIAO perturbation method employing the nucleus independent chemical shift (NICS) concept and the results visualized as iso\u2010chemical\u2010shielding surfaces (ICSS) of various size and direction. The synergy of geometry (linear or bent, orthogonal or twisted structures) and NMR characteristics (extend of the high field shift of the central carbon atom, anisotropy effect of the <jats:italic>allene\u2010like<\/jats:italic> C=C double bonds or the <jats:italic>ball\u2010like<\/jats:italic> anisotropy effect of <jats:italic>carbone\u2010like<\/jats:italic> central carbon atom) provides a comprehensive picture of the <jats:italic>dominating resonance contributor<\/jats:italic>.<\/jats:p>","DOI":"10.1002\/asia.202300826","type":"journal-article","created":{"date-parts":[[2023,11,15]],"date-time":"2023-11-15T14:14:40Z","timestamp":1700057680000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Carbones \u2013 A Classification on the Magnetic Criterion"],"prefix":"10.1002","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8993-0033","authenticated-orcid":false,"given":"Erich","family":"Kleinpeter","sequence":"first","affiliation":[{"name":"Chemisches Institut der Universit\u00e4t Potsdam  Karl-Liebknecht-Str. 24\u201325 D-14476 Potsdam (Golm) Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas","family":"Koch","sequence":"additional","affiliation":[{"name":"Chemisches Institut der Universit\u00e4t Potsdam  Karl-Liebknecht-Str. 24\u201325 D-14476 Potsdam (Golm) Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,12,28]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.200800208"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1351\/PAC-CON-08-11-03"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39940002517"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2015.01.007"},{"key":"e_1_2_7_6_1","unstructured":"\u00a0"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197605021"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/om020753p"},{"key":"e_1_2_7_9_1","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.248"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201101213"},{"key":"e_1_2_7_12_1","unstructured":"\u00a0"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200602552"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701632"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200701390"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700139"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0dt01555e"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/bs.adomc.2017.08.002"},{"key":"e_1_2_7_19_1","first-page":"1893","author":"Klod S.","year":"2001","journal-title":"J. Chem. Soc. Perkin Trans. 2"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.theochem.2007.02.049"},{"key":"e_1_2_7_21_1","unstructured":"\u00a0"},{"key":"e_1_2_7_22_2","doi-asserted-by":"crossref","unstructured":"E. Kleinpeter inAnnual Reports on NMR Spectroscopy (edited by Graham A. Webb) ELSEVIER Vol. 82 (2014) \u2013 Chapter\u20053: Quantification and Visualization of the Anisotropy Effect in NMR Spectroscopy by Through-Space NMR Shieldings;","DOI":"10.1016\/B978-0-12-800184-4.00003-5"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.4979"},{"key":"e_1_2_7_24_1","unstructured":"The quantum chemical calculations were performed using the Gaussian 09 program package[53]and carried out on LINUX clusters. The studied structures were fully optimized at the MP2\/6\u2013311G(d p) level of theory without constraints.[54]The obtained structures have been confirmed as local minima by performing harmonic frequency calculations at the optimized geometries.[55]NICS values[56 57]were computed on the basis of the MP2\/6\u2013311G(d p) geometries using the gauge-including atomic orbital (GIAO) method[58 59]at the B3LYP\/6\u2013311G(d p)[60\u201362]theory level.[63]Variation of the basis set was found to be of non-significant influence on the NICS values. To calculate the spatial NICS ghost atoms were placed on a lattice of \u221210\u2005\u00c5 to +10\u2005\u00c5 with a step size of 0.5\u2005\u00c5 in the three directions of the Cartesian coordinate system. The zero points of the coordinate system were positioned at the centers of the studied structures. The resulting 68 921 NICS values thus obtained were analyzed and visualized by the SYBYL 7.3 molecular modeling software;[64]different iso-chemical-shielding surfaces (ICSS) of \u22120.5\u2005ppm (orange) and \u22120.1\u2005ppm (red) deshielding and 5\u2005ppm (blue) 2\u2005ppm (cyan) 0.5\u2005ppm (green) and 0.1\u2005ppm (yellow) shielding were used to visualize the TS\u2005NMRSs of the studied structures in the various figures. ICSSs are a quantitative indication of the anisotropy and ring current effect in1H NMR spectroscopy;[11\u201313]the computed shielding(deshielding) ICSSs quantify the corresponding anisotropy\/ring current effect in1H NMR spectroscopy subject to the distance from the center of the molecules (in \u00c5).[11\u201313]."},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp300860q"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01477a052"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)81750-7"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00493a035"},{"key":"e_1_2_7_29_1","unstructured":"\u00a0"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19790910520"},{"key":"e_1_2_7_31_2","doi-asserted-by":"crossref","unstructured":"R. Appel U. Baumeister F. Knoch Chem. 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Only if DFT or HF calculations are applied this is true; in case of electron correlation calculations the \u201cghost atoms\u201d get their own electron density and show some influence on the energy of the studied molecule. In these cases the TS\u2005NMRS surfaces are heavily distorted."},{"key":"e_1_2_7_90_1","unstructured":"SYBYL 7.3 Tripos Inc. 1699 South Hanley Road St. Louis Missouri 63144 USA 2007."}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202300826","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T18:30:14Z","timestamp":1759948214000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.202300826"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12,28]]},"references-count":90,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2024,1,15]]}},"alternative-id":["10.1002\/asia.202300826"],"URL":"https:\/\/doi.org\/10.1002\/asia.202300826","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"type":"print","value":"1861-4728"},{"type":"electronic","value":"1861-471X"}],"subject":[],"published":{"date-parts":[[2023,12,28]]},"assertion":[{"value":"2023-09-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-12-28","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202300826"}}