Table 1.

The Gibbs free energies computed for all dimerisation interactions with respect to the most stable tautomer ADDA in implicit chloroform solvation at the BLYP‐D3(BJ)/TZ2P level of theory (without alkyl chains).

Hydrogen‐bonding motif	Interacting array	ΔG [kcal mol−1]
Homodimers
AUPy	ADAD[a]	−2.2
AUPy	AADD	0.6
UPy	ADAD	−2.6
UPy	AADD[a]	−6.9
NAPyO	ADAD[a]	−3.5
NAPyO	AADD	7.4
Heterodimers
AUPy⋅DAN	ADDA⋅DAAD[a]	−5.0
UPy⋅DAN	ADDA⋅DAAD[a]	−4.8
AUPy⋅NAPyO	ADAD⋅DADA[a]	−2.3
AUPy⋅NAPyO	AADD⋅DDAA	4.1
AUPy⋅NAPyO	ADDA⋅DAAD	0.0
UPy⋅NAPyO	ADAD⋅DADA	−2.6
UPy⋅NAPyO	AADD⋅DDAA	0.8
UPy⋅NAPyO	ADDA⋅DAAD	0.5
AUPy⋅UPy	ADAD⋅DADA	−2.4
AUPy⋅UPy	AADD⋅DDAA	−3.1

[a] Interacting array of dimers seen experimentally.