Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization

IF 3.7 Q2 CHEMISTRY, PHYSICAL ACS Physical Chemistry Au Pub Date : 2023-08-31 DOI:10.1021/acsphyschemau.3c00029
Robert Fraczkiewicz*, 
{"title":"Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization","authors":"Robert Fraczkiewicz*,&nbsp;","doi":"10.1021/acsphyschemau.3c00029","DOIUrl":null,"url":null,"abstract":"<p >We discovered an anomalous basic dissociation in certain multiprotic compounds. An amine group placed in the middle of a given compound is predicted to behave unusually─at certain pH ranges, its averaged degree of protonation actually <i>increases</i> with pH (!) resulting from interactions with other ionizable groups. This chameleonic behavior results in two p<i>K</i><sub>50</sub> values: one corresponding to a weaker base and the other to a stronger base for the same group.</p>","PeriodicalId":29796,"journal":{"name":"ACS Physical Chemistry Au","volume":null,"pages":null},"PeriodicalIF":3.7000,"publicationDate":"2023-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsphyschemau.3c00029","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Physical Chemistry Au","FirstCategoryId":"1085","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsphyschemau.3c00029","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0

Abstract

We discovered an anomalous basic dissociation in certain multiprotic compounds. An amine group placed in the middle of a given compound is predicted to behave unusually─at certain pH ranges, its averaged degree of protonation actually increases with pH (!) resulting from interactions with other ionizable groups. This chameleonic behavior results in two pK50 values: one corresponding to a weaker base and the other to a stronger base for the same group.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
胺能同时成为弱碱和强碱吗?变色龙电离的奇怪案例
我们在某些多质子化合物中发现了反常的碱性解离。在特定的pH值范围内,由于与其他可电离基团的相互作用,它的平均质子化程度实际上随着pH值的增加而增加。这种变色龙行为导致两个pK50值:一个对应于较弱的碱基,另一个对应于同一群体的较强的碱基。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
CiteScore
3.70
自引率
0.00%
发文量
0
期刊介绍: ACS Physical Chemistry Au is an open access journal which publishes original fundamental and applied research on all aspects of physical chemistry. The journal publishes new and original experimental computational and theoretical research of interest to physical chemists biophysical chemists chemical physicists physicists material scientists and engineers. An essential criterion for acceptance is that the manuscript provides new physical insight or develops new tools and methods of general interest. Some major topical areas include:Molecules Clusters and Aerosols; Biophysics Biomaterials Liquids and Soft Matter; Energy Materials and Catalysis
期刊最新文献
Issue Publication Information Issue Editorial Masthead Roundabout Mechanism of Ion–Molecule Nucleophilic Substitution Reactions Ultrafast Spin Relaxation of Charge Carriers in Strongly Quantum Confined Methylammonium Lead Bromide Perovskite Magic-Sized Clusters Direct Detection of Bound Water in Hydrated Powders of Lysozyme by Differential Scanning Calorimetry
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1