{"id":"https://openalex.org/W2014313320","doi":"https://doi.org/10.1107/s0108270108008275","title":"1,3-Bis(ethylamino)-2-nitrobenzene, 1,3-bis(n-octylamino)-2-nitrobenzene and 4-ethylamino-2-methyl-1H-benzimidazole","display_name":"1,3-Bis(ethylamino)-2-nitrobenzene, 1,3-bis(n-octylamino)-2-nitrobenzene and 4-ethylamino-2-methyl-1H-benzimidazole","publication_year":2008,"publication_date":"2008-04-08","ids":{"openalex":"https://openalex.org/W2014313320","doi":"https://doi.org/10.1107/s0108270108008275","mag":"2014313320","pmid":"https://pubmed.ncbi.nlm.nih.gov/18451479"},"language":"en","primary_location":{"id":"doi:10.1107/s0108270108008275","doi":"https://doi.org/10.1107/s0108270108008275","is_oa":false,"landing_page_url":"https://doi.org/10.1107/s0108270108008275","pdf_url":null,"source":{"id":"https://openalex.org/S149116045","display_name":"Acta Crystallographica Section C Crystal Structure Communications","issn_l":"0108-2701","issn":["0108-2701","1600-5759"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Acta Crystallographica Section C Crystal Structure Communications","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5073609432","display_name":"Christopher Paul Walczak","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1629065","display_name":"Central Michigan University","ror":"https://ror.org/02xawj266","country_code":"US","type":"education","lineage":["https://openalex.org/I1629065"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Christopher P. Walczak","raw_affiliation_strings":["Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859, USA","institution_ids":["https://openalex.org/I1629065"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5022669438","display_name":"Matthew M. Yonkey","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1629065","display_name":"Central Michigan University","ror":"https://ror.org/02xawj266","country_code":"US","type":"education","lineage":["https://openalex.org/I1629065"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Matthew M. Yonkey","raw_affiliation_strings":["Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859 (USA)"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859 (USA)","institution_ids":["https://openalex.org/I1629065"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5086735650","display_name":"Philip J. Squattrito","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1629065","display_name":"Central Michigan University","ror":"https://ror.org/02xawj266","country_code":"US","type":"education","lineage":["https://openalex.org/I1629065"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Philip J. Squattrito","raw_affiliation_strings":["Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859, USA","institution_ids":["https://openalex.org/I1629065"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5104005036","display_name":"Dillip K Mohanty","orcid":"https://orcid.org/0000-0002-8275-0627","observed_orcids":["https://orcid.org/0000-0002-8275-0627"]},"institutions":[{"id":"https://openalex.org/I1629065","display_name":"Central Michigan University","ror":"https://ror.org/02xawj266","country_code":"US","type":"education","lineage":["https://openalex.org/I1629065"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Dillip K. Mohanty","raw_affiliation_strings":["Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859, USA","institution_ids":["https://openalex.org/I1629065"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5071694801","display_name":"Kristin Kirschbaum","orcid":"https://orcid.org/0000-0003-4206-0610","observed_orcids":["https://orcid.org/0000-0003-4206-0610"]},"institutions":[{"id":"https://openalex.org/I90871651","display_name":"University of Toledo","ror":"https://ror.org/01pbdzh19","country_code":"US","type":"education","lineage":["https://openalex.org/I90871651"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Kristin Kirschbaum","raw_affiliation_strings":["Department of Chemistry, University of Toledo, Toledo, OH 43606, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Toledo, Toledo, OH 43606, USA","institution_ids":["https://openalex.org/I90871651"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":3760,"currency":"USD","value_usd":3760},"apc_paid":null,"fwci":0.404,"has_fulltext":false,"cited_by_count":5,"citation_normalized_percentile":{"value":0.63212376,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":96},"biblio":{"volume":"64","issue":"5","first_page":"o248","last_page":"o251"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10464","display_name":"Crystal structures of chemical compounds","score":0.9556000232696533,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10464","display_name":"Crystal structures of chemical compounds","score":0.9556000232696533,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":0.030300000682473183,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12410","display_name":"Structural and Chemical Analysis of Organic and Inorganic Compounds","score":0.0035000001080334187,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/nitrobenzene","display_name":"nitrobenzene","score":0.7129999995231628},{"id":"https://openalex.org/keywords/benzimidazole","display_name":"benzimidazole","score":0.8080000281333923},{"id":"https://openalex.org/keywords/intramolecular-hydrogen-bonding","display_name":"intramolecular hydrogen bonding","score":0.8090000152587891},{"id":"https://openalex.org/keywords/hydrophobic-interactions","display_name":"hydrophobic interactions","score":0.7519999742507935},{"id":"https://openalex.org/keywords/crystal-packing","display_name":"crystal packing","score":0.6019999980926514},{"id":"https://openalex.org/keywords/thermal-cyclization","display_name":"thermal cyclization","score":0.6909999847412109},{"id":"https://openalex.org/keywords/n-hn-hydrogen-bonds","display_name":"N-H\u22efN hydrogen bonds","score":0.7379999756813049},{"id":"https://openalex.org/keywords/polymers","display_name":"polymers","score":0.5329999923706055}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8649278879165649},{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.7152107357978821},{"id":"https://openalex.org/C2780809723","wikidata":"https://www.wikidata.org/wiki/Q407290","display_name":"Nitrobenzene","level":3,"score":0.7053256034851074},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.6342161893844604},{"id":"https://openalex.org/C2778484023","wikidata":"https://www.wikidata.org/wiki/Q415190","display_name":"Benzimidazole","level":2,"score":0.6101735830307007},{"id":"https://openalex.org/C2780639532","wikidata":"https://www.wikidata.org/wiki/Q7041427","display_name":"Nitro","level":3,"score":0.5941316485404968},{"id":"https://openalex.org/C2780874372","wikidata":"https://www.wikidata.org/wiki/Q328692","display_name":"Imidazole","level":2,"score":0.5663846731185913},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.5623504519462585},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.5189430713653564},{"id":"https://openalex.org/C2777691172","wikidata":"https://www.wikidata.org/wiki/Q2270","display_name":"Benzene","level":2,"score":0.49420788884162903},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.38290664553642273},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.34835803508758545},{"id":"https://openalex.org/C8010536","wikidata":"https://www.wikidata.org/wiki/Q160398","display_name":"Crystallography","level":1,"score":0.3326651453971863},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.14831849932670593},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1107/s0108270108008275","doi":"https://doi.org/10.1107/s0108270108008275","is_oa":false,"landing_page_url":"https://doi.org/10.1107/s0108270108008275","pdf_url":null,"source":{"id":"https://openalex.org/S149116045","display_name":"Acta Crystallographica Section C Crystal Structure Communications","issn_l":"0108-2701","issn":["0108-2701","1600-5759"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Acta Crystallographica Section C Crystal Structure Communications","raw_type":"journal-article"},{"id":"pmid:18451479","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/18451479","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Acta crystallographica. Section C, Crystal structure communications","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":4,"referenced_works":["https://openalex.org/W1973921447","https://openalex.org/W2015276069","https://openalex.org/W2021651548","https://openalex.org/W2131350133"],"related_works":["https://openalex.org/W2084440539","https://openalex.org/W2006829829","https://openalex.org/W2000886430","https://openalex.org/W1277063722","https://openalex.org/W3151697660","https://openalex.org/W101438848","https://openalex.org/W2203118274","https://openalex.org/W1536305151","https://openalex.org/W4245888567","https://openalex.org/W1129934967"],"abstract_inverted_index":{"1,3-Bis(ethylamino)-2-nitrobenzene,":[0],"C(10)H(15)N(3)O(2),":[1],"(I),":[2],"and":[3,22,25,44,83,114,187],"1,3-bis(n-octylamino)-2-nitrobenzene,":[4],"C(22)H(39)N(3)O(2),":[5],"(II),":[6],"are":[7,15,89,152],"the":[8,18,23,29,42,70,79,94,105,161,165,177],"first":[9,178],"structurally":[10],"characterized":[11],"1,3-bis(n-alkylamino)-2-nitrobenzenes.":[12],"Both":[13,35],"molecules":[14,55,88,144,151],"bisected":[16],"though":[17],"nitro":[19,45],"N":[20],"atom":[21],"2-C":[24],"5-C":[26],"atoms":[27],"of":[28,90,97,107,120,181],"ring":[30],"by":[31,66,75],"twofold":[32],"rotation":[33],"axes.":[34],"display":[36],"intramolecular":[37],"N-H...O":[38],"hydrogen":[39,50,121,158,173],"bonds":[40,159],"between":[41,78],"amine":[43],"groups,":[46],"but":[47],"no":[48,146],"intermolecular":[49,84],"bonding.":[51,174],"The":[52,81,150],"nearly":[53],"planar":[54],"pack":[56],"into":[57,154],"flat":[58],"layers":[59],"ca":[60],"3.4":[61],"A":[62],"apart":[63],"that":[64],"interact":[65],"hydrophobic":[67],"interactions":[68,77,85],"involving":[69,160],"n-alkyl":[71],"groups":[72,167],"rather":[73],"than":[74],"pi-pi":[76],"rings.":[80],"intra-":[82],"in":[86,92,104,111,171],"these":[87,136],"interest":[91],"understanding":[93],"physical":[95],"properties":[96],"polymers":[98],"made":[99],"from":[100,133],"them.":[101],"Upon":[102],"heating":[103],"presence":[106],"anhydrous":[108],"potassium":[109],"carbonate":[110],"dimethylacetamide,":[112],"(I)":[113,134],"(II)":[115],"cyclize":[116],"with":[117,145,185],"formal":[118],"loss":[119],"peroxide":[122],"to":[123],"form":[124],"substituted":[125],"benzimidazoles.":[126],"Thus,":[127],"4-ethylamino-2-methyl-1H-benzimidazole,":[128],"C(10)H(13)N(3),":[129],"(III),":[130],"was":[131],"obtained":[132],"under":[135],"reaction":[137],"conditions.":[138],"Compound":[139],"(III)":[140],"contains":[141],"two":[142],"independent":[143],"imposed":[147],"internal":[148],"symmetry.":[149],"linked":[153],"chains":[155],"via":[156],"N-H...N":[157],"imidazole":[162],"rings,":[163],"while":[164],"ethylamino":[166],"do":[168],"not":[169],"participate":[170],"any":[172],"This":[175],"is":[176],"reported":[179],"structure":[180],"a":[182],"benzimidazole":[183],"derivative":[184],"4-amino":[186],"2-alkyl":[188],"substituents.":[189]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":1}],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2016-06-24T00:00:00"}