Correlations between steric/thermochemical parameters and O-/N-acylation reactions of cellulose

► O-acylation of cellulose using β-Ala gave the highest DS% compared to Gly and α,l-Ala. ► β-Ala-Cellulose is the most reactive to give highest N-acylation yield. ► Thermochemical/strain transitions in O-/N-acylation of cellotetraose-model. ► The lower steric energy of β-Ala-Cellulose is advantageous for N-acylation.