{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,23]],"date-time":"2026-06-23T21:42:59Z","timestamp":1782250979992,"version":"3.54.5"},"reference-count":98,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2022,12,19]],"date-time":"2022-12-19T00:00:00Z","timestamp":1671408000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2023,2,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The oxidative addition of C\u2212C bonds in aromatic hydrocarbons by low valent main group species has attracted considerable attention from both theoretical and experimental chemists due to the big challenge in breaking their aromaticity. Herein, a general strategy to break the C\u2212C bonds in benzene by cyclic (alkyl)(amino)aluminyl anion is demonstrated via density functional theory (DFT) calculations. The results suggest that the activation of the C\u2212C bond of benzene by this anion is both kinetically and thermodynamically unfavorable whereas introducing electron\u2010withdrawing groups makes such C\u2212C bond activation becomes favorable both kinetically and thermodynamically. Such a sharp change on the kinetics and thermodynamics could be rationalized by the frontier molecular orbital theory by decreasing the lowest unoccupied molecular orbitals of the mono\u2010 and disubstituted benzenes. Aromaticity is found to stabilize the transition state for the ring open step. All these findings can help develop the chemistry of small\u2010molecule activation.<\/jats:p>","DOI":"10.1002\/chem.202203216","type":"journal-article","created":{"date-parts":[[2022,11,9]],"date-time":"2022-11-09T04:49:47Z","timestamp":1667969387000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Probing a General Strategy to Break the C\u2212C Bond of Benzene by a Cyclic (Alkyl)(Amino)Aluminyl Anion"],"prefix":"10.1002","volume":"29","author":[{"given":"Fangzhou","family":"Xu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM) Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry Department of Chemistry College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2099-3156","authenticated-orcid":false,"given":"Jun","family":"Zhu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM) Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry Department of Chemistry College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,12,19]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00092"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/tf9625802285"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408034"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201408034"},{"key":"e_1_2_8_4_1","unstructured":"\u00a0"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/364676a0"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0157-x"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00031"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201900443"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527680092"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-021-03801-y"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b05925"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.188501802119"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/C39750000723"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc32150e"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b01562"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611409"},{"key":"e_1_2_8_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201611409"},{"key":"e_1_2_8_18_1","unstructured":"\u00a0"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00121"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809984k"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature13624"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b09264"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007543"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201007543"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja034478p"},{"key":"e_1_2_8_25_1","unstructured":"\u00a0"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b05136"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205785"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja970588i"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b11791"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c02724"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature08634"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199105641"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19911030527"},{"key":"e_1_2_8_33_1","unstructured":"\u00a0"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20001201)39:23<4274::AID-ANIE4274>3.0.CO;2-K"},{"key":"e_1_2_8_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20001201)112:23<4444::AID-ANGE4444>3.0.CO;2-U"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja003185i"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202011594"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202011594"},{"key":"e_1_2_8_37_1","unstructured":"\u00a0"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201809236"},{"key":"e_1_2_8_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201809236"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202006693"},{"key":"e_1_2_8_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202006693"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201811675"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201811675"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201914986"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201914986"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c03179"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-019-0365-z"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-018-0037-y"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202000921"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.0c00444"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211800"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c07389"},{"key":"e_1_2_8_49_1","unstructured":"\u00a0"},{"key":"e_1_2_8_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c10222"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c02463"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202111975"},{"key":"e_1_2_8_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202111975"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202116658"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202202102"},{"key":"e_1_2_8_55_1","author":"Zhang X.","year":"2022","journal-title":"CCS"},{"key":"e_1_2_8_56_1","unstructured":"\u00a0"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201900294"},{"key":"e_1_2_8_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.1c00438"},{"key":"e_1_2_8_59_1","unstructured":"\u00a0"},{"key":"e_1_2_8_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201900010"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.0c01754"},{"key":"e_1_2_8_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.0c03520"},{"key":"e_1_2_8_63_1","unstructured":"\u00a0"},{"key":"e_1_2_8_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201901415"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701486"},{"key":"e_1_2_8_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201701486"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b11564"},{"key":"e_1_2_8_67_1","unstructured":"\u00a0"},{"key":"e_1_2_8_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201801220"},{"key":"e_1_2_8_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1469"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030088"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201500897"},{"key":"e_1_2_8_72_1","unstructured":"M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A.\u2005V. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Jr. Montgomery J.\u2005E. Peralta F. Ogliaro M.\u2005J. Bearpark J.\u2005J. Heyd E.\u2005N. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T.\u2005A. Keith R. Kobayashi J. Normand K. Raghavachari A.\u2005P. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman D.\u2005J.Fox Gaussian 16 Revision A.03; Gaussian: Wallingford CT USA 2016."},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.463096"},{"key":"e_1_2_8_75_1","unstructured":"\u00a0"},{"key":"e_1_2_8_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100717a029"},{"key":"e_1_2_8_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00072a001"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct200106a"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.467146"},{"key":"e_1_2_8_80_1","unstructured":"\u00a0"},{"key":"e_1_2_8_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/0301-0104(81)85090-2"},{"key":"e_1_2_8_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540151009"},{"key":"e_1_2_8_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp9716997"},{"key":"e_1_2_8_84_1","unstructured":"E.\u2005D. Glendening J.\u2005K. Badenhoop A.\u2005E. Reed J.\u2005E. Carpenter J.\u2005A. Bohmann C.\u2005M. Morales C.\u2005R. Landis F. Weinhold NBO 7.0; Theoretical Chemistry Institute University of Wisconsin: Madison WI 2013.http:\/\/nbo7.chem.wisc.edu\/."},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.2834918"},{"key":"e_1_2_8_86_1","unstructured":"C.\u2005Y. Legault CYLview 1.0b ed.; Universit\u00e9 de Sherbrooke: Sherbrooke Quebec Canada 2009;http:\/\/www.cylview.org."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203216","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202203216","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203216","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T10:50:40Z","timestamp":1760266240000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202203216"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,19]]},"references-count":98,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2023,2,7]]}},"alternative-id":["10.1002\/chem.202203216"],"URL":"https:\/\/doi.org\/10.1002\/chem.202203216","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,19]]},"assertion":[{"value":"2022-10-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-12-19","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202203216"}}