d-glucose is a strategic chemical for agri-food and pharma industries, which are now exploiting an expected increase of 5% in the global investment round from 2020 to 2028. Despite such a broad industrial interest, the reasons behind room-p monomorphism in d-glucose are unclear. The crystal structure of α-d-glucose is provided here with an unprecedented resolution (0.46 Å) by single-crystal X-ray diffraction at T = 90(1) K. Occurrence of anomeric disorder in the α phase, which has not been reported to date, is demonstrated. The topological analysis of the total charge density distribution is also carried out within the framework of Bader's Quantum Theory of Atoms in Molecules, allowing to rank the relative strength of hydrogen bonds in the crystal structure. It is found that most OH···O contacts have a significant covalent character and build up an exceptionally stiff three-dimensional hydrogen bond network. On the one hand, this locks the molecular conformation by hampering the rotational flexibility of the hydroxy substituents. On the other hand, favorable recognition modes, based on the interaction of the charge density distributions of glucose molecules, cooperatively account for the lattice cohesion. A change in the relative orientation of OH groups would affect the crystal cohesion by changing locally the molecular electrostatic potential, V(r).

Why Is α- D -Glucose Monomorphic? Insights from Accurate Experimental Charge Density at 90 K / L. Sironi, S. Rizzato, L. Lo Presti. - In: CRYSTAL GROWTH & DESIGN. - ISSN 1528-7483. - 22:11(2022), pp. 6627-6638. [10.1021/acs.cgd.2c00846]

Why Is α- D -Glucose Monomorphic? Insights from Accurate Experimental Charge Density at 90 K

L. Sironi
Primo
Investigation
;
S. Rizzato
Investigation
;
L. Lo Presti
Ultimo
Supervision
2022

Abstract

d-glucose is a strategic chemical for agri-food and pharma industries, which are now exploiting an expected increase of 5% in the global investment round from 2020 to 2028. Despite such a broad industrial interest, the reasons behind room-p monomorphism in d-glucose are unclear. The crystal structure of α-d-glucose is provided here with an unprecedented resolution (0.46 Å) by single-crystal X-ray diffraction at T = 90(1) K. Occurrence of anomeric disorder in the α phase, which has not been reported to date, is demonstrated. The topological analysis of the total charge density distribution is also carried out within the framework of Bader's Quantum Theory of Atoms in Molecules, allowing to rank the relative strength of hydrogen bonds in the crystal structure. It is found that most OH···O contacts have a significant covalent character and build up an exceptionally stiff three-dimensional hydrogen bond network. On the one hand, this locks the molecular conformation by hampering the rotational flexibility of the hydroxy substituents. On the other hand, favorable recognition modes, based on the interaction of the charge density distributions of glucose molecules, cooperatively account for the lattice cohesion. A change in the relative orientation of OH groups would affect the crystal cohesion by changing locally the molecular electrostatic potential, V(r).
Settore CHIM/02 - Chimica Fisica
Settore CHIM/06 - Chimica Organica
Settore CHIM/03 - Chimica Generale e Inorganica
Article (author)
File in questo prodotto:
File Dimensione Formato  
Sironi_Rizzato_Lo-Presti_Crystal_Growth_Des_2022_just_accepted.pdf

embargo fino al 20/10/2023

Tipologia: Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione 6.98 MB
Formato Adobe PDF
6.98 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
acs.cgd.2c00846.pdf

accesso riservato

Tipologia: Publisher's version/PDF
Dimensione 7.16 MB
Formato Adobe PDF
7.16 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/946360
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? ND
social impact