Table 1.
Molecular electrostatic potential on the acidic atom nucleus, experimental pKa data and valence NAO energies for amines and anilines (N-containing) calculated at the B3LYP/6−311+G(2d,2p) level of theory. Atomic units.
| Compounds | MEP@N | Exp. pKa | NAO px | NAO py | NAO pz |
|---|---|---|---|---|---|
| Et2NCH | −18.33812 | −2.0 | −0.2591 | −0.2587 | −0.2649 |
| Diethylcyanimide | −18.33841 | 1.2 | −0.2576 | −0.2577 | −0.2647 |
| Acetanilide | −18.34462 | 0.61 | −0.2602 | −0.2556 | −0.2744 |
| NCH2CH2CN3 | −18.34761 | 1.1 | −0.2553 | −0.2538 | −0.2699 |
| HNCH2CN2 | −18.34941 | 0.2 | −0.2449 | −0.2439 | −0.2700 |
| p-Nitrobenzne | −18.35054 | 1.02 | −0.2808 | −0.2539 | −0.2432 |
| EtNCH2CN2 | −18.35225 | −0.6 | −0.2439 | −0.2488 | −0.2598 |
| 3-Methyl-4-nitrobenzene | −18.35365 | 1.5 | −0.2495 | −0.2400 | −0.2782 |
| 4-Chloro-3-nitrobenzene | −18.35567 | 1.9 | −0.2450 | −0.2396 | −0.2758 |
| p-Cyanobenzene | −18.35809 | 1.74 | −0.2734 | −0.2456 | −0.2358 |
| 35-Dimethyl-4-nitrobenzene | −18.36144 | 2.59 | −0.2415 | −0.2323 | −0.2698 |
| m-Nitrobenzene | −18.36192 | 2.5 | −0.2369 | −0.2361 | −0.2698 |
| m-Cyanobenzene | −18.36429 | 2.76 | −0.2345 | −0.2335 | −0.2673 |
| 35-Dibromobenzene | −18.36433 | 2.34 | −0.2303 | −0.2386 | −0.2671 |
| 35-Dichloro-aniline | −18.36477 | 2.37 | −0.2294 | −0.2379 | −0.2666 |
| 3-Methoxy-5-nitrobenzene | −18.36538 | 2.11 | −0.2288 | −0.2367 | −0.2664 |
| 4-Methyl-3-nitrobenzene | −18.36640 | 2.96 | −0.2328 | −0.2294 | −0.2657 |
| 35-Dibromo-4-methoxybenzene | −18.36833 | 2.98 | −0.2258 | −0.2353 | −0.2609 |
| EtNCH2CH2CN2 | −18.36848 | 4.55 | −0.2304 | −0.2426 | −0.2426 |
| 35-Dibromo-4-methylbenzene | −18.36912 | 2.87 | −0.2253 | −0.2327 | −0.2622 |
| Dicyanodiethylamine | −18.36961 | 5.2 | −0.2247 | −0.2261 | −0.2614 |
| HNCH2CH2CN2 | −18.37007 | 5.26 | −0.2360 | −0.2517 | −0.2239 |
| 35-Dibromo-4-hydroxybenzene | −18.37157 | 3.2 | −0.2225 | −0.2292 | −0.2594 |
| PhNMe2 | −18.37325 | 5.1 | −0.2264 | −0.2261 | −0.2335 |
| Dimethylaminoacetonitrile | −18.37434 | 4.2 | −0.2215 | −0.2206 | −0.2435 |
| m-Bromobenzene | −18.37435 | 3.51 | −0.2240 | −0.2243 | −0.2574 |
| 3-Choloro-aniline | −18.37477 | 3.52 | −0.2242 | −0.2229 | −0.2570 |
| m-Chlorobenzene | −18.37477 | 3.34 | −0.2242 | −0.2229 | −0.2570 |
| p-Bromobenzene | −18.37538 | 3.91 | −0.2271 | −0.2185 | −0.2562 |
| m-Fluorobenzene | −18.37572 | 3.59 | −0.2252 | −0.2199 | −0.2560 |
| 3-Fluoro-aniline | −18.37572 | 3.58 | −0.2252 | −0.2199 | −0.2560 |
| 2-Choloro-aniline | −18.37606 | 2.64 | −0.2229 | −0.2240 | −0.2558 |
| 4-Choloro-aniline | −18.37636 | 3.99 | −0.2260 | −0.2175 | −0.2553 |
| p-Chlorobenzene | −18.37636 | 3.98 | −0.2552 | −0.2261 | −0.2175 |
| 2-Fluoro-aniline | −18.37697 | 3.2 | −0.2222 | −0.2186 | −0.2537 |
| PhNEt2 | −18.37729 | 6.6 | −0.2271 | −0.2230 | −0.2306 |
| 3-Chloro-5-methoxybenzene | −18.37780 | 3.1 | −0.2170 | −0.2237 | −0.2538 |
| 3-Bromo-4-methylbenzene | −18.37862 | 3.98 | −0.2199 | −0.2188 | −0.2529 |
| 3-Chloro-4-methylbenzene | −18.37907 | 4.05 | −0.2213 | −0.2162 | −0.2524 |
| CF3CH2N(CH3)2 | −18.38004 | 4.75 | −0.2200 | −0.2169 | −0.2358 |
| 4-Fluoro-aniline | −18.38037 | 4.65 | −0.2214 | −0.2134 | −0.2512 |
| p-Fluorobenzene | −18.38037 | 4.65 | −0.2510 | −0.2216 | −0.2134 |
| Diethylaminoacetonitrile | −18.38089 | 4.5 | −0.2153 | −0.2156 | −0.2405 |
| n-Piperidine-CH2CN | −18.38182 | 4.55 | −0.2370 | −0.2196 | −0.2164 |
| Aminoacetonitrile | −18.38220 | 5.3 | −0.2131 | −0.2222 | −0.2422 |
| H2NCH2CN | −18.38220 | 5.34 | −0.2131 | −0.2222 | −0.2422 |
| 3-Bromo-4-methoxybenzene | −18.38280 | 4.08 | −0.2160 | −0.2129 | −0.2484 |
| Et2NCH2CN | −18.38315 | 4.55 | −0.2150 | −0.2213 | −0.2302 |
| Beta-dimethylaminopropionitrile | −18.38334 | 7.0 | −0.2132 | −0.2147 | −0.2379 |
| m-Hydroxybenzene | −18.38508 | 4.17 | −0.2158 | −0.2104 | −0.2468 |
| Aniline | −18.38581 | 4.58 | −0.2460 | −0.2171 | −0.2078 |
| 35-Dimethoxybenzene | −18.38610 | 3.82 | −0.2072 | −0.2164 | −0.2456 |
| CF3CH2NHCH3 | −18.38635 | 6.05 | −0.2172 | −0.2356 | −0.2054 |
| n-Piperidine-CCH3CN | −18.38648 | 9.22 | −0.2131 | −0.2111 | −0.2345 |
| CF3CH2NH2 | −18.38776 | 5.7 | −0.2105 | −0.2225 | −0.2334 |
| 3-Methoxyl-aniline | −18.38807 | 4.2 | −0.2120 | −0.2080 | −0.2438 |
| m-Methoxybenzene | −18.38807 | 4.2 | −0.2120 | −0.2080 | −0.2438 |
| m-Methylbenzene | −18.38808 | 4.69 | −0.2118 | −0.2078 | −0.2442 |
| Et2NC(CH3)2CN | −18.38892 | 9.13 | −0.2132 | −0.2152 | −0.2278 |
| 4-Methyl-aninile | −18.38929 | 5.08 | −0.2127 | −0.2041 | −0.2426 |
| p-Methylbenzene | −18.38929 | 5.12 | −0.2127 | −0.2041 | −0.2426 |
| n-Methyleamphetamine-(CH2)2CN | −18.38970 | 6.95 | −0.2235 | −0.2194 | −0.2149 |
| p-Hydroxybenzene | −18.38980 | 5.5 | −0.2113 | −0.2036 | −0.2416 |
| Et2N(CH2)2CN | −18.38981 | 7.65 | −0.2236 | −0.2098 | −0.2185 |
| 35-dimethylbenzene | −18.39012 | 4.91 | −0.2032 | −0.2132 | −0.2408 |
| m-Aminobenzene | −18.39058 | 4.88 | −0.2401 | −0.2062 | −0.2099 |
| 34-Dimethylbenzene | −18.39133 | 5.17 | −0.2101 | −0.2025 | −0.2404 |
| Beta-diethylaminopropionitrile | −18.39143 | 7.6 | −0.2083 | −0.2145 | −0.2247 |
| 2-Amino-2-cyanopropane | −18.39167 | 5.3 | −0.2083 | −0.2261 | −0.2214 |
| 4-Methoxyl-aniline | −18.39174 | 5.36 | −0.2105 | −0.2037 | −0.2363 |
| p-Methoxybenzene | −18.39174 | 5.29 | −0.2093 | −0.2017 | −0.2397 |
| Beta-aminopropionitrile | −18.39304 | 7.7 | −0.2045 | −0.2237 | −0.2235 |
| Phenyl_OHOHOHH | −18.39345 | 8.58 | −0.2052 | −0.2034 | −0.2490 |
| n-Amphetamine-(CH2)2CN | −18.39407 | 7.23 | −0.2031 | −0.2009 | −0.2390 |
| Epinephrine | −18.39415 | 8.55 | −0.2037 | −0.2082 | −0.2311 |
| 3-Amino-4-hydroxybenzene | −18.39512 | 5.7 | −0.2066 | −0.1988 | −0.2352 |
| p-Aminobenzene | −18.39595 | 6.08 | −0.2049 | −0.1972 | −0.2352 |
| Triethanolamine | −18.39601 | 7.77 | −0.2013 | −0.2013 | −0.2265 |
| Arterenol | −18.39616 | 8.55 | −0.2080 | −0.2286 | −0.2127 |
| Et2N(CH2)3CN | −18.39621 | 9.29 | −0.2048 | −0.2040 | −0.2221 |
| 2-Methyleanilne-Et2 | −18.39666 | 7.18 | −0.2021 | −0.2068 | −0.2168 |
| n-Methylmorpholine | −18.39918 | 7.41 | −0.2213 | −0.2059 | −0.1981 |
| n-Allylmorpholine | −18.39975 | 7.05 | −0.2057 | −0.1994 | −0.2200 |
| nn-Dimethyl-2−2-aminoethoxyethanol | −18.40040 | 9.1 | −0.1961 | −0.1968 | −0.2199 |
| Et2N(CH2)4CN | −18.40046 | 10.08 | −0.2171 | −0.2020 | −0.1992 |
| n-Benzoylpiperazine | −18.40053 | 7.78 | −0.1995 | −0.1954 | −0.2259 |
| Beta-difluoroethylamine | −18.40078 | 7.52 | −0.1947 | −0.2375 | −0.1934 |
| Triallylamine | −18.40090 | 8.31 | −0.2141 | −0.2036 | −0.2028 |
| Dimethylethanolamine | −18.40128 | 10.3 | −0.1984 | −0.1966 | −0.2157 |
| n-Ethylmorpholine | −18.40141 | 7.7 | −0.1999 | −0.1975 | −0.2229 |
| Benzyldimethylamine | −18.40151 | 8.93 | −0.1980 | −0.2175 | −0.1954 |
| Et2N(CH2)5CN | −18.40182 | 10.46 | −0.2068 | −0.2020 | −0.2067 |
| Allyldimethylamine | −18.40272 | 8.72 | −0.1945 | −0.1943 | −0.2155 |
| Diallylmethylamine | −18.40366 | 8.79 | −0.1940 | −0.1989 | −0.2138 |
| n-Carbethoxypiperazine | −18.40371 | 8.28 | −0.1972 | −0.1896 | −0.2246 |
| (CH3)3N | −18.40449 | 9.76 | −0.1920 | −0.1920 | −0.2165 |
| Morpholine | −18.40649 | 8.36 | −0.2266 | −0.1900 | −0.1864 |
| Alpha-benzylpyrroline | −18.40658 | 7.08 | −0.2027 | −0.2096 | −0.1946 |
| n-Allylpiperidine | −18.40716 | 9.69 | −0.1915 | −0.1915 | −0.2156 |
| Triethylenediamine | −18.40816 | 8.8 | −0.2232 | −0.1849 | −0.1849 |
| Benzyldiethylamine | −18.40854 | 9.48 | −0.1925 | −0.1982 | −0.2000 |
| Ethanolamine | −18.40857 | 9.5 | −0.2035 | −0.1917 | −0.2085 |
| Diallylamine | −18.40900 | 9.29 | −0.1851 | −0.2090 | −0.1964 |
| n-Methylpiperidine | −18.40921 | 10.08 | −0.1921 | −0.1888 | −0.2137 |
| Dimethyl-n-propylamine | −18.40975 | 9.99 | −0.2059 | −0.1935 | −0.1897 |
| Dimethylethylamine | −18.40982 | 9.99 | −0.2122 | −0.1881 | −0.1896 |
| Dimethyl-n-butylamine | −18.40987 | 10.02 | −0.2058 | −0.1931 | −0.1894 |
| Benzylmethylamine | −18.40990 | 9.58 | −0.1984 | −0.1980 | −0.1922 |
| n-Methylpyrrolidine | −18.41092 | 10.46 | −0.1933 | −0.1872 | −0.2151 |
| Allylmethylamine | −18.41106 | 10.11 | −0.1840 | −0.1799 | −0.2186 |
| 1n-Propylpiperidine | −18.41122 | 10.48 | −0.1882 | −0.1880 | −0.2124 |
| n-Methyltrimethyleneimine | −18.41175 | 10.4 | −0.2146 | −0.1886 | −0.1822 |
| nn-Dimethylcyclohexylamine | −18.41175 | 10.0 | −0.1880 | −0.2009 | −0.1949 |
| 2−2-Aminoethoxyethanol | −18.41184 | 9.5 | −0.2142 | −0.1957 | −0.1804 |
| Methyldiethylamine | −18.41187 | 10.29 | −0.1904 | −0.1890 | −0.2055 |
| 12-Dimethylpyrrolidine | −18.41198 | 10.26 | −0.1905 | −0.1899 | −0.2141 |
| Benzylethylamine | −18.41266 | 9.68 | −0.1935 | −0.1817 | −0.2097 |
| (CH3)2NH | −18.41295 | 10.64 | −0.1972 | −0.1984 | −0.1805 |
| Benzylamine | −18.41331 | 9.34 | −0.1858 | −0.2148 | −0.1899 |
| Alpha-ethylpyrroline | −18.41335 | 7.43 | −0.2103 | −0.1905 | −0.1864 |
| (C2H5)3N | −18.41377 | 10.65 | −0.1880 | −0.1898 | −0.2031 |
| n-Ethylpiperidine | −18.41388 | 10.4 | −0.2055 | −0.1933 | −0.1871 |
| (C3H7)3N | −18.41393 | 10.65 | −0.1859 | −0.1870 | −0.2043 |
| (C4H9)3N | −18.41423 | 10.89 | −0.1860 | −0.1877 | −0.2011 |
| Allylamine | −18.41470 | 9.49 | −0.1821 | −0.2101 | −0.1925 |
| Quinuclidine | −18.41526 | 11.0 | −0.1784 | −0.1793 | −0.2155 |
| Phenyl_HHHH | −18.41548 | 9.78 | −0.1815 | −0.1869 | −0.2123 |
| Beta-Phenylethylamine | −18.41599 | 9.83 | −0.1835 | −0.2026 | −0.1958 |
| Methoxypropylamine | −18.41712 | 10.1 | −0.1786 | −0.1910 | −0.2078 |
| Phenyl_ohohohch3 | −18.41714 | 8.55 | −0.1840 | −0.1757 | −0.2045 |
| Ethylenediamine | −18.41724 | 9.98 | −0.2037 | −0.1961 | −0.1754 |
| Piperidine | −18.41752 | 11.22 | −0.1781 | −0.1762 | −0.2156 |
| Gama-Phenylpropylamine | −18.41761 | 10.2 | −0.1779 | −0.2052 | −0.1929 |
| Diisobutylamine | −18.41775 | 10.5 | −0.2177 | −0.1766 | −0.1763 |
| i_(C3H7)3N | −18.41776 | 11.05 | −0.1827 | −0.1822 | −0.2029 |
| CH3NH2 | −18.41803 | 10.62 | −0.2121 | −0.1870 | −0.1735 |
| (C2H5)2NH | −18.41862 | 10.98 | −0.1815 | −0.1868 | −0.1949 |
| NH3 | −18.41865 | 9.21 | −0.1827 | −0.1827 | −0.2301 |
| (C3H7)2NH | −18.41886 | 11.0 | −0.1898 | −0.1843 | −0.1897 |
| Pyrrolidine | −18.41906 | 11.27 | −0.1752 | −0.1790 | −0.2161 |
| (C4H9)2NH | −18.41920 | 11.25 | −0.1925 | −0.1789 | −0.1884 |
| Trimethyleneimine | −18.41950 | 11.29 | −0.2115 | −0.1780 | −0.1745 |
| 1-Ethylr-2-methylpyrrolidine | −18.41964 | 10.64 | −0.1926 | −0.1873 | −0.2037 |
| C2H5NH2 | −18.42005 | 10.63 | −0.2052 | −0.1899 | −0.1730 |
| C3H7NH2 | −18.42022 | 10.53 | −0.2001 | −0.1937 | −0.1728 |
| C4H9NH2 | −18.42049 | 10.59 | −0.2073 | −0.1857 | −0.1724 |
| Phenyl_HHOHH | −18.42093 | 8.9 | −0.1749 | −0.1782 | −0.2127 |
| i_(C3H7)2NH | −18.42188 | 11.0 | −0.1761 | −0.1941 | −0.1906 |
| i_C3H7NH2 | −18.42234 | 10.63 | −0.1932 | −0.1948 | −0.1775 |
| Phenyl_HOHOHH | −18.42246 | 8.93 | −0.1776 | −0.1933 | −0.1943 |
| Cyclohexylaime | −18.42277 | 9.82 | −0.2120 | −0.1806 | −0.1712 |
| Cyclohexylamine | −18.42277 | 10.49 | −0.2120 | −0.1806 | −0.1712 |
| Di-sec-butylamine | −18.42332 | 11.01 | −0.1732 | −0.2087 | −0.1774 |
| Cycloheptylamine | −18.42339 | 9.99 | −0.1740 | −0.1709 | −0.2184 |