AUTHOR=Zhu Huajie , Li Shengnan , Jia Yunjing , Jiang Juxing , Hu Feiliu , Li Longfei , Cao Fei , Wang Xiaoke , Li Shenhui , Ouyang Guanghui , Tian Gengfang , Gong Ke , Hou Guangjin , He Wei , Zhao Zheng , Pittman Charles U. , Deng Feng , Liu Minghua , Sun Kai , Tang Ben Zhong TITLE=Pseudo-resonance structures in chiral alcohols and amines and their possible aggregation states JOURNAL=Frontiers in Chemistry VOLUME=10 YEAR=2022 URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.964615 DOI=10.3389/fchem.2022.964615 ISSN=2296-2646 ABSTRACT=

We now report that some chiral compounds, like alcohols, which are not sterically hindered atropisomers nor epimer mixtures, exhibit two sets of simultaneous NMR spectra in CDCl3. Some other chiral alcohols also simultaneously exhibit two different NMR spectra in the solid state because two different conformers, A and B had different sizes because their corresponding bond lengths and angles are different. These structures were confirmed in the same solid state by X-ray. We designate these as pseudo-resonance for a compound exhibiting several different corresponding lengths that simultaneously coexist in the solid state or liquid state. Variable-temperature NMR, 2D NMR methods, X-ray, neutron diffraction, IR, photo-luminesce (PL) and other methods were explored to study whether new aggregation states caused these heretofore unknown pseudo-resonance structures. Finally, eleven chiral alcohols or diols were found to co-exist in pseudo-resonance structures by X-ray crystallography in a search of the CDS database.