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. Author manuscript; available in PMC: 2018 Jul 26.
Published in final edited form as: J Am Chem Soc. 2017 Jul 17;139(29):9885–9894. doi: 10.1021/jacs.7b03261

Table 1.

Strengths of Interaction (α-values) of Alkyl Ureas with Amide and Hydrocarbon Unified Atomsa

Unfied atom α (cal mol−1 molal−1 Å−2)b
Solute Amide O Amide N Aliphatic sp3C Amide sp2C Aromatic sp2C
urea −0.52 ±0.04 −0.09 ±0.02 −0.07 ±0.01 −0.69 ±0.06 −0.59 ±0.01
mu 0.52 ±0.08 −0.44 ±0.03 −0.31 ±0.01 −0.99 ±0.07 −1.37 ±0.08
eu 0.79 ±0.06 −0.55 ±0.02 −0.43 ±0.01 −1.2 ±0.05 −1.62 ±0.07
1,1 -dmu 1.09 ±0.07 −0.61 ±0.03 −0.35 ±0.01 −1.53 ±0.05 −2.05 ±0.08
1,3-dmu 1.68 ±0.09 −0.77 ±0.03 −0.56 ±0.01 −1.87 ±0.06 −1.97 ±0.04
1,1-deu 1.73 ±0.09 −0.84 ±0.03 −0.64 ±0.01 −1.88 ±0.07 −2.72 ±0.1
1,3-deu 2.35 ±0.09 −1.01 ±0.04 −0.76 ±0.01 −2.28 ±0.07 −2.97 ±0.13
naphthalene −4.44 ± 0.8 0.85 ±0.29 −2.71 ±0.07 −2.88 ±0.83 ---c
a

Solute abbreviations: mu: methylurea; eu: ethylurea; dmu: dimethylurea; deu: diethylurea;

b

α-values are obtained by fitting experimental μ23 values (Tables S2 and S3) for amide-amide interactions to Equations 3, and for amide-aromatic interactions to Equation 4. Propagated uncertainties in α-values are calculated as described previously.19

c

Not determined.