Solvent-assisted monomeric molecular structure of the phosphate diester and the synthesis of menthol-based phosphate diesters
DEBDEEP MANDAL VIVEK GUPTA BISWAJIT SANTRA NICOLAS CHRYSOCHOS VIVEK W BHOYARE AVIJIT MAITI ABHISEK KAR SUMAN ANKU GUHA PALLAVI THAKUR RAMAKIRUSHNAN SURIYA NARAYANAN NITIN T PATIL CAROLA SCHULZKE VADAPALLI CHANDRASEKHAR ANUKUL JANA
Phosphate diesters are well known to form intermolecular H-bonded dimeric structures in their solid-state. Recently, we reported 2,6-(CHPh)2-4-iPr-phenyl substituted phosphate diester exists as H-bonded monomeric molecular structure along with water dimer in the solid-state. Herein we report 2,6-(CHPh)2-4-iPr-phenyl substituted phosphate diester forms a monomeric molecular structure in the solid-state upon cocrystallization with dimethylformamide, DMF(Me2NCHO). The -CHO group of DMF simultaneously acts as an H-bond acceptor to P-OH and an H-bond donor to P=O moieties. We also used the alcohols, ROH (R = Me, Et, iPr, and tBu), for crystallisation of 2,6-(CHPh)2-4-iPr-phenyl substituted phosphate diester. In these instances, solvent-incorporated dimeric structures are found in the solid-state. We also report the syntheses and molecular structures of anionic phosphate diesters of 2,6-(CHPh)2-4-iPr-phenyl substitutedphosphate diester possessing various counter cations. Moreover, we also report the syntheses and molecular structures of phosphate diesters based on (-)-menthol, (?)-menthol and (?)/(-)-menthol. These exist as H-bonded dimers in the solid-state.
DEBDEEP MANDAL1 VIVEK GUPTA1 BISWAJIT SANTRA1 NICOLAS CHRYSOCHOS2 VIVEK W BHOYARE3 AVIJIT MAITI1 ABHISEK KAR1 SUMAN1 ANKU GUHA1 PALLAVI THAKUR1 RAMAKIRUSHNAN SURIYA NARAYANAN1 NITIN T PATIL3 CAROLA SCHULZKE2 VADAPALLI CHANDRASEKHAR1 4 ANUKUL JANA1
Volume 134, 2022
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