{"doi":"10.1002/ejoc.200600445","title":"<i>C</i><sub>2</sub>‐Chiral Substituted <i>cis</i>‐1,3,5,7‐Tetraazadecalins as Proton Sponges:A Computational Study","abstract":"<jats:title>Abstract</jats:title><jats:p>Density functional quantum chemical calculations at the B3LYP/6‐31+G* and B3LYP/6‐31+G** levels have been performed to calculate the proton affinities of chiral <jats:italic>cis</jats:italic>‐1,5‐diazadecalins <jats:bold>1</jats:bold>,<jats:bold>2</jats:bold> and substituted <jats:italic>cis</jats:italic>‐1,3,5,7‐tetraazadecalin <jats:bold>3</jats:bold>. The calculated gas‐phase proton affinities of <jats:italic>cis</jats:italic>‐1,3,5,7‐tetraazadecalins are higher than that of 1,8‐bis(dimethylamino)naphthalene (<jats:bold>4</jats:bold>). <jats:italic>cis</jats:italic>‐1,5‐Diazadecalins show lower proton affinities compared with those of substituted 1,3,5,7‐tetraazadecalins. Cooperative and anomeric effects seem to be responsible for the additional stabilization of the protonated forms of 1,3,5,7‐tetraazadecalins. Intramolecular proton transfer energies have been predicted for these amines and discussed. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2006)</jats:p>","journal":"European Journal of Organic Chemistry","year":2006,"id":44269,"datarank":0.7513395554865647,"base_score":2.9444389791664403,"endowment":2.9444389791664403,"self_citation_contribution":0.44166584687496613,"citation_network_contribution":0.30967370861159854,"self_endowment_contribution":0.44166584687496613,"citer_contribution":0.30967370861159854,"corpus_percentile":null,"corpus_rank":null,"citation_count":18,"citer_count":11,"citers_with_citation_signal":10,"citers_with_endowment":10,"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":208709,"name":"Shampa Chakraborty","orcid":null,"position":1,"is_corresponding":false},{"id":208710,"name":"Bishwajit Ganguly","orcid":null,"position":2,"is_corresponding":false},{"id":208708,"name":"Ajeet Singh","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":2.9444389791664403,"endowment":2.9444389791664403,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"21464855","pmcid":null,"openalex_id":"https://openalex.org/W2067738646","authors":[],"funders":[],"total_grants":0,"fwci":0.8362,"citation_percentile":0.72362142,"influential_citations":0,"citation_trend":[{"year":2012,"count":2},{"year":2013,"count":3},{"year":2014,"count":2},{"year":2016,"count":2},{"year":2017,"count":1},{"year":2018,"count":2},{"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%2Fejoc.200600445","host_type":"publisher"},{"url":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.200600445","host_type":"publisher"},{"url":"https://doi.org/10.1002/ejoc.200600445","host_type":"journal"}],"fields_of_study":["Chemical Reaction Mechanisms","DNA and Nucleic Acid Chemistry","Supramolecular Chemistry and Complexes","Chemistry"],"mesh_terms":[],"keywords":["Chemistry","Affinities","Protonation","Intramolecular force","Proton","Proton affinity","Computational chemistry","Quantum chemical","Gas phase","Density functional theory","Naphthalene","Stereochemistry","Medicinal chemistry","Physical chemistry","Organic chemistry","Molecule","Ion"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-18T02:13:50.014940Z","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":[]}