{"doi":"10.1002/poc.1760","title":"Investigation of the substituent specific cross‐interaction effects on <sup>13</sup>C NMR of the CN bridging group in substituted benzylidene anilines","abstract":"<jats:title>Abstract</jats:title><jats:p>The substituent effect on <jats:sup>13</jats:sup>C NMR of the CN in benzylidene anilines XPhCHNPhY was investigated, in which the substituents X and Y are in <jats:italic>p</jats:italic>‐position or in <jats:italic>m</jats:italic>‐position of the two aromatic rings. The substituent effects including the inductive effects of X and Y, the conjugative effects of X and Y, and the substituent specific cross‐interaction effect were put into one model to quantify the <jats:sup>13</jats:sup>C NMR chemical shift <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN) of the CN in XPhCHNPhY. A penta‐parameter correlation equation with correlation coefficient 0.9975 and standard error 0.17 ppm was obtained for 80 samples of compounds. The result shows that the substituents X and Y have an opposite effect on the <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN). The electron‐withdrawing effects of X decrease the <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN); while the electron‐donating effects of X increase the <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN). In contrast, the electron‐withdrawing effects of Y increase the <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN); while the electron‐donating effects of Y decrease the <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN). A new substituent specific cross‐interaction effect parameter Δ<jats:italic>σ</jats:italic><jats:sup>2</jats:sup> was proposed, which indicates that the most substituent specific cross‐interaction effect exists in the pair of max electron‐withdrawing group (EWG) and max electron‐donating group (EDG) or the pair of max EDG and max EWG. Further to verify the obtained correlation equation, 15 samples of model compounds were prepared and their <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN) was measured in this work. The predicted <jats:italic>δ</jats:italic><jats:sub>C</jats:sub>(CN) values with the obtained equation are in good agreement with the measured ones for these prepared compounds, which confirmed the reliability of the obtained equation. Copyright © 2010 John Wiley &amp; Sons, Ltd.</jats:p>","journal":"Journal of Physical Organic Chemistry","year":2011,"id":42555,"datarank":2.3664648456688777,"base_score":3.6635616461296463,"endowment":3.6635616461296463,"self_citation_contribution":0.5495342469194471,"citation_network_contribution":1.8169305987494304,"self_endowment_contribution":0.5495342469194471,"citer_contribution":1.8169305987494304,"corpus_percentile":null,"corpus_rank":null,"citation_count":38,"citer_count":32,"citers_with_citation_signal":31,"citers_with_endowment":31,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":203547,"name":"Bingtao Lu","orcid":null,"position":1,"is_corresponding":false},{"id":203548,"name":"Guanfan Chen","orcid":null,"position":2,"is_corresponding":false},{"id":203546,"name":"Chenzhong Cao","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":3.6635616461296463,"endowment":3.6635616461296463,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"18998881","pmcid":null,"openalex_id":"https://openalex.org/W2078189959","authors":[],"funders":[],"total_grants":0,"fwci":1.5213,"citation_percentile":0.81221246,"influential_citations":0,"citation_trend":[{"year":2012,"count":6},{"year":2013,"count":2},{"year":2014,"count":4},{"year":2015,"count":2},{"year":2016,"count":5},{"year":2017,"count":4},{"year":2018,"count":3},{"year":2019,"count":3},{"year":2020,"count":3},{"year":2021,"count":2},{"year":2022,"count":1},{"year":2023,"count":1},{"year":2025,"count":1}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpoc.1760","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/poc.1760","host_type":"publisher"},{"url":"https://doi.org/10.1002/poc.1760","host_type":"journal"}],"fields_of_study":["Structural and Chemical Analysis of Organic and Inorganic Compounds","Synthesis of heterocyclic compounds","Chemical Reaction Mechanisms","Chemistry"],"mesh_terms":[],"keywords":["Substituent","Chemistry","Polar effect","Chemical shift","Carbon-13 NMR","Stereochemistry","Proton NMR","Crystallography","Medicinal chemistry","Physical chemistry"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-14T03:41:06.262380Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}