Internal rotation formamide

K. B. Wiberg and C. M. Breneman,/. Am. Chem. Soc., 114, 831 (1992). Resonance Interactions in Acyclic Systems. 3. Formamide Internal Rotation Revisited. Charge and Energy Redistribution along the C—N Bond Rotational Pathway. 

Interactions in Acyclic Systems. 3. Formamide Internal Rotation Revisited. Charge and Energy Redistribution Along the C—N Bond Rotational Pathway. 

An understanding of the internal rotation about the amide bond is important because of its relevance to protein structure. Formamide is the simplest amide. The coplanarity and the remarkable rotational barrier about the C-N bond in formamide can be rationalized by resonance between the n electrons of the carbonyl group and the lone pair of the nitrogen atom [1, 50]. According to VB theory, the Jt electronic structure of formamide may be described by six resonance structures. 

Chen W, Gordon MS. The effective fragment model for solvation internal rotation in formamide. J Chem Phys 1996 105 11081-11090. 

Chen, W., Gordon, M. S. (1996]. The Effective Fragment Model for Solvation Internal Rotation In Formamide,/. Chem. Phys., 105,11081-11090. 

S. Tsuzuki and K. Tanabe, /. Chem. Soc., Perkin Trans. 2, 1255 (1991). Basis Set and Electron Correlation Effects on die Internal Rotational Barrier Heights of Formamide and Acetamide. 

The rate of internal rotations is often strongly solvent dependent. One of the simplest molecules to exhibit such behaviour is formamide, whose equilibrium geometry is planar, with two barriers to its internal rotation (transition states TSl and TS2), corresponding to the geometries shown in Figure 3. 

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