CIESC Journal ›› 2020, Vol. 71 ›› Issue (S1): 15-22.DOI: 10.11949/0438-1157.20191380
• Thermodynamics • Previous Articles Next Articles
Jiaxin LIU1(),Yu XU1,Er HUA1,2,3()
Received:
2019-11-13
Revised:
2019-12-19
Online:
2020-04-25
Published:
2020-04-25
Contact:
Er HUA
通讯作者:
花儿
作者简介:
刘佳鑫(1995—),女,硕士研究生,基金资助:
CLC Number:
Jiaxin LIU, Yu XU, Er HUA. Structure and hydrogen bonding study on acylamino acid protic ionic liquids composed of 2-N-ethylhexylethylenediaminim cation with acylalanineate anions[J]. CIESC Journal, 2020, 71(S1): 15-22.
刘佳鑫, 徐宇, 花儿. 异辛基乙二胺-酰基丙氨酸型质子化离子液体的分子间氢键相互作用[J]. 化工学报, 2020, 71(S1): 15-22.
Structure | N—H bond | r/? | Δr/? |
---|---|---|---|
[HEtHex]1+ | N31—H33 | 1.0238 | |
N31—H32 | 1.0245 | ||
[HEtHex]2+ | N34—H35 | 1.0252 | |
[HEtHex][Butala]S1 | N31—H33 | 1.6519 | 0.6281 |
[HEtHex][Butala]S2 | N31—H33 | 1.6302 | 0.6064 |
[HEtHex][Butala]S3 | N31—H32 | 1.6513 | 0.6268 |
[HEtHex][Butala]S4 | N34—H35 | 1.5928 | 0.5676 |
[HEtHex][Butala]S5 | N34—H35 | 1.5743 | 0.5491 |
[HEtHex][Hexala]S1 | N31—H33 | 1.6528 | 0.6290 |
[HEtHex][Hexala]S2 | N31—H33 | 1.6304 | 0.6066 |
[HEtHex][Hexala]S3 | N31—H32 | 1.6508 | 0.6263 |
[HEtHex][Hexala]S4 | N34—H35 | 1.6107 | 0.5855 |
[HEtHex][Hexala]S5 | N34—H35 | 1.5775 | 0.5523 |
Table 1 Bond lengths (r) for isolated cations and [HEtHex][Acylala] S1—S5 structures
Structure | N—H bond | r/? | Δr/? |
---|---|---|---|
[HEtHex]1+ | N31—H33 | 1.0238 | |
N31—H32 | 1.0245 | ||
[HEtHex]2+ | N34—H35 | 1.0252 | |
[HEtHex][Butala]S1 | N31—H33 | 1.6519 | 0.6281 |
[HEtHex][Butala]S2 | N31—H33 | 1.6302 | 0.6064 |
[HEtHex][Butala]S3 | N31—H32 | 1.6513 | 0.6268 |
[HEtHex][Butala]S4 | N34—H35 | 1.5928 | 0.5676 |
[HEtHex][Butala]S5 | N34—H35 | 1.5743 | 0.5491 |
[HEtHex][Hexala]S1 | N31—H33 | 1.6528 | 0.6290 |
[HEtHex][Hexala]S2 | N31—H33 | 1.6304 | 0.6066 |
[HEtHex][Hexala]S3 | N31—H32 | 1.6508 | 0.6263 |
[HEtHex][Hexala]S4 | N34—H35 | 1.6107 | 0.5855 |
[HEtHex][Hexala]S5 | N34—H35 | 1.5775 | 0.5523 |
Structure | ?E0/(kcal?mol-1) | ?E0BSSE/(kcal?mol-1) | Structure | ?E0/(kcal?mol-1) | ?E0BSSE/(kcal?mol-1) |
---|---|---|---|---|---|
[HEtHex][Butala]S1 | -133.38 | -128.68 | [HEtHex][Hexala]S1 | -133.31 | -128.63 |
[HEtHex][Butala]S2 | -132.05 | -127.33 | [HEtHex][Hexala]S2 | -131.97 | -127.25 |
[HEtHex][Butala]S3 | -142.15 | -136.14 | [HEtHex][Hexala]S3 | -133.11 | -127.01 |
[HEtHex][Butala]S4 | -123.78 | -117.26 | [HEtHex][Hexala]S4 | -125.43 | -119.03 |
[HEtHex][Butala]S5 | -124.15 | -117.66 | [HEtHex][Hexala]S5 | -124.11 | -117.57 |
Table 2 Interaction energies ΔE0 for [HEtHex][Acylal] at M06-2X/6-311G(d,p) level
Structure | ?E0/(kcal?mol-1) | ?E0BSSE/(kcal?mol-1) | Structure | ?E0/(kcal?mol-1) | ?E0BSSE/(kcal?mol-1) |
---|---|---|---|---|---|
[HEtHex][Butala]S1 | -133.38 | -128.68 | [HEtHex][Hexala]S1 | -133.31 | -128.63 |
[HEtHex][Butala]S2 | -132.05 | -127.33 | [HEtHex][Hexala]S2 | -131.97 | -127.25 |
[HEtHex][Butala]S3 | -142.15 | -136.14 | [HEtHex][Hexala]S3 | -133.11 | -127.01 |
[HEtHex][Butala]S4 | -123.78 | -117.26 | [HEtHex][Hexala]S4 | -125.43 | -119.03 |
[HEtHex][Butala]S5 | -124.15 | -117.66 | [HEtHex][Hexala]S5 | -124.11 | -117.57 |
Structure | O—H bond | ν/cm-1 | Δν/cm-1 |
---|---|---|---|
[Butala] | O—H | 3832.81 | |
[Hexala] | O—H | 3832.02 | |
[HEtHex][Butala]S1 | O57—H33 | 2812.78 | 1020.03 |
[HEtHex][Butala]S2 | O58—H33 | 2715.63 | 1117.18 |
[HEtHex][Butala]S3 | O58—H32 | 2679.84 | 1152.97 |
[HEtHex][Butala]S4 | O58—H35 | 2472.57 | 1360.24 |
[HEtHex][Butala]S5 | O58—H35 | 2401.35 | 1431.46 |
[HEtHex][Hexala]S1 | O57—H33 | 2813.06 | 1018.96 |
[HEtHex][Hexala]S2 | O58—H33 | 2712.18 | 1119.84 |
[HEtHex][Hexala]S3 | O58—H32 | 2686.96 | 1145.06 |
[HEtHex][Hexala]S4 | O57—H35 | 2565.97 | 1266.05 |
[HEtHex][Hexala]S5 | O58—H35 | 2410.52 | 1421.50 |
Table 3 O—H vibrational frequencies ν and red shift Δν for [HEtHex][Acylala]S1—S5
Structure | O—H bond | ν/cm-1 | Δν/cm-1 |
---|---|---|---|
[Butala] | O—H | 3832.81 | |
[Hexala] | O—H | 3832.02 | |
[HEtHex][Butala]S1 | O57—H33 | 2812.78 | 1020.03 |
[HEtHex][Butala]S2 | O58—H33 | 2715.63 | 1117.18 |
[HEtHex][Butala]S3 | O58—H32 | 2679.84 | 1152.97 |
[HEtHex][Butala]S4 | O58—H35 | 2472.57 | 1360.24 |
[HEtHex][Butala]S5 | O58—H35 | 2401.35 | 1431.46 |
[HEtHex][Hexala]S1 | O57—H33 | 2813.06 | 1018.96 |
[HEtHex][Hexala]S2 | O58—H33 | 2712.18 | 1119.84 |
[HEtHex][Hexala]S3 | O58—H32 | 2686.96 | 1145.06 |
[HEtHex][Hexala]S4 | O57—H35 | 2565.97 | 1266.05 |
[HEtHex][Hexala]S5 | O58—H35 | 2410.52 | 1421.50 |
Bond | N31 | N34 | H32 | H33 | H35 | O57 | O58 | O59 |
---|---|---|---|---|---|---|---|---|
[Butala]- | -0.780 | -0.816 | -0.707 | |||||
[Hexala]- | -0.780 | -0.816 | -0.707 | |||||
[HEtHex]1+ | -0.690 | -0.689 | 0.437 | 0.444 | 0.358 | |||
[HEtHex]2+ | -0.827 | -0.554 | 0.364 | 0.364 | 0.424 | |||
[HEtHex][Butala]S1 | -0.873 | -0.687 | 0.365 | 0.514 | 0.341 | -0.734 | -0.681 | -0.66 |
[HEtHex][Butala]S2 | -0.871 | -0.689 | 0.381 | 0.517 | 0.344 | -0.664 | -0.76 | -0.659 |
[HEtHex][Butala]S3 | -0.869 | -0.691 | 0.517 | 0.372 | 0.365 | -0.668 | -0.767 | -0.66 |
[HEtHex][Butala]S4 | -0.834 | -0.719 | 0.34 | 0.34 | 0.513 | -0.668 | -0.774 | -0.659 |
[HEtHex][Butala]S5 | -0.834 | -0.708 | 0.344 | 0.34 | 0.512 | -0.663 | -0.777 | -0.659 |
[HEtHex][Hexala]S1 | -0.873 | -0.687 | 0.365 | 0.514 | 0.341 | -0.681 | -0.734 | -0.66 |
[HEtHex][Hexala]S2 | -0.871 | -0.689 | 0.381 | 0.517 | 0.344 | -0.664 | -0.76 | -0.659 |
[HEtHex][Hexala]S3 | -0.869 | -0.692 | 0.517 | 0.372 | 0.368 | -0.671 | -0.765 | -0.658 |
[HEtHex][Hexala]S4 | -0.834 | -0.719 | 0.341 | 0.34 | 0.511 | -0.746 | -0.688 | -0.661 |
[HEtHex][Hexala]S5 | -0.834 | -0.708 | 0.344 | 0.34 | 0.512 | -0.664 | -0.776 | -0.659 |
Table 4 Partial charges for main hydrogen bonding of [HEtHex][Acylala] at M06-2X/6-311G(d, p) level/e
Bond | N31 | N34 | H32 | H33 | H35 | O57 | O58 | O59 |
---|---|---|---|---|---|---|---|---|
[Butala]- | -0.780 | -0.816 | -0.707 | |||||
[Hexala]- | -0.780 | -0.816 | -0.707 | |||||
[HEtHex]1+ | -0.690 | -0.689 | 0.437 | 0.444 | 0.358 | |||
[HEtHex]2+ | -0.827 | -0.554 | 0.364 | 0.364 | 0.424 | |||
[HEtHex][Butala]S1 | -0.873 | -0.687 | 0.365 | 0.514 | 0.341 | -0.734 | -0.681 | -0.66 |
[HEtHex][Butala]S2 | -0.871 | -0.689 | 0.381 | 0.517 | 0.344 | -0.664 | -0.76 | -0.659 |
[HEtHex][Butala]S3 | -0.869 | -0.691 | 0.517 | 0.372 | 0.365 | -0.668 | -0.767 | -0.66 |
[HEtHex][Butala]S4 | -0.834 | -0.719 | 0.34 | 0.34 | 0.513 | -0.668 | -0.774 | -0.659 |
[HEtHex][Butala]S5 | -0.834 | -0.708 | 0.344 | 0.34 | 0.512 | -0.663 | -0.777 | -0.659 |
[HEtHex][Hexala]S1 | -0.873 | -0.687 | 0.365 | 0.514 | 0.341 | -0.681 | -0.734 | -0.66 |
[HEtHex][Hexala]S2 | -0.871 | -0.689 | 0.381 | 0.517 | 0.344 | -0.664 | -0.76 | -0.659 |
[HEtHex][Hexala]S3 | -0.869 | -0.692 | 0.517 | 0.372 | 0.368 | -0.671 | -0.765 | -0.658 |
[HEtHex][Hexala]S4 | -0.834 | -0.719 | 0.341 | 0.34 | 0.511 | -0.746 | -0.688 | -0.661 |
[HEtHex][Hexala]S5 | -0.834 | -0.708 | 0.344 | 0.34 | 0.512 | -0.664 | -0.776 | -0.659 |
Structure | Charge transfer | E(2) | Structure | Charge transfer | E(2) |
---|---|---|---|---|---|
[HEtHex][Butala]S1 | LP(N31)→σ*(H33-O57) | 43.67 | [HEtHex][Hexala]S1 | LP(N31)→σ*(H33-O57) | 43.58 |
[HEtHex][Butala]S2 | LP(N31)→σ*(H33-O58) | 47.74 | [HEtHex][Hexala]S2 | LP(N31)→σ*(H33-O58) | 47.72 |
[HEtHex][Butala]S3 | LP(N31)→σ*(H32-O58) | 47.33 | [HEtHex][Hexala]S3 | LP(N31)→σ*(H32-O58) | 47.48 |
[HEtHex][Butala]S4 | LP(N34)→σ*(H35-O58) | 54.49 | [HEtHex][Hexala]S4 | LP(N34)→σ*(H35-O57) | 50.85 |
[HEtHex][Butala]S5 | LP(N34)→σ*(H35-O58) | 57.58 | [HEtHex][Hexala]S5 | LP(N34)→σ*(H35-O58) | 56.86 |
Table 5 Second-order interaction energies E(2) between lp(N) and σ*(H—O) in all complexes [HEtHex][Acylala] calculated at M06-2X/6-311G(d,p) level/(kcal?mol-1)
Structure | Charge transfer | E(2) | Structure | Charge transfer | E(2) |
---|---|---|---|---|---|
[HEtHex][Butala]S1 | LP(N31)→σ*(H33-O57) | 43.67 | [HEtHex][Hexala]S1 | LP(N31)→σ*(H33-O57) | 43.58 |
[HEtHex][Butala]S2 | LP(N31)→σ*(H33-O58) | 47.74 | [HEtHex][Hexala]S2 | LP(N31)→σ*(H33-O58) | 47.72 |
[HEtHex][Butala]S3 | LP(N31)→σ*(H32-O58) | 47.33 | [HEtHex][Hexala]S3 | LP(N31)→σ*(H32-O58) | 47.48 |
[HEtHex][Butala]S4 | LP(N34)→σ*(H35-O58) | 54.49 | [HEtHex][Hexala]S4 | LP(N34)→σ*(H35-O57) | 50.85 |
[HEtHex][Butala]S5 | LP(N34)→σ*(H35-O58) | 57.58 | [HEtHex][Hexala]S5 | LP(N34)→σ*(H35-O58) | 56.86 |
Structure | BCP | ρc/a.u. | ?2ρc/a.u. | G(r)/a.u. | V(r)/a.u. | H(r)/a.u. | EHB/(kcal?mol-1) |
---|---|---|---|---|---|---|---|
[HEtHex][Butala]S1 | N31…H33—O57 | 0.061 | 0.101 | 0.043 | -0.06 | -0.017 | 18.76 |
[HEtHex][Butala]S2 | N31…H33—O58 | 0.065 | 0.098 | 0.044 | -0.064 | -0.02 | 20.06 |
[HEtHex][Butala]S3 | N31…H32—O58 | 0.062 | 0.095 | 0.042 | -0.06 | -0.018 | 18.69 |
[HEtHex][Butala]S4 | N34…H35—O58 | 0.073 | 0.086 | 0.047 | -0.073 | -0.026 | 22.87 |
[HEtHex][Butala]S5 | N34…H35—O58 | 0.076 | 0.083 | 0.049 | -0.077 | -0.028 | 24.19 |
[HEtHex][Hexala]S1 | N31…H33—O57 | 0.061 | 0.101 | 0.042 | -0.06 | -0.017 | 18.72 |
[HEtHex][Hexala]S2 | N31…H33—O58 | 0.065 | 0.098 | 0.044 | -0.064 | -0.02 | 20.06 |
[HEtHex][Hexala]S3 | N31…H32—O58 | 0.062 | 0.095 | 0.042 | -0.06 | -0.018 | 18.74 |
[HEtHex][Hexala]S4 | N34…H35—O57 | 0.070 | 0.090 | 0.046 | -0.069 | -0.023 | 21.70 |
[HEtHex][Hexala]S5 | N34…H35—O58 | 0.076 | 0.083 | 0.049 | -0.076 | -0.028 | 23.95 |
Table 6 Properties of electron density of BCP for configurations of [HEtHex][Acylala] calculated at M06-2X/6-311G(d,p) level
Structure | BCP | ρc/a.u. | ?2ρc/a.u. | G(r)/a.u. | V(r)/a.u. | H(r)/a.u. | EHB/(kcal?mol-1) |
---|---|---|---|---|---|---|---|
[HEtHex][Butala]S1 | N31…H33—O57 | 0.061 | 0.101 | 0.043 | -0.06 | -0.017 | 18.76 |
[HEtHex][Butala]S2 | N31…H33—O58 | 0.065 | 0.098 | 0.044 | -0.064 | -0.02 | 20.06 |
[HEtHex][Butala]S3 | N31…H32—O58 | 0.062 | 0.095 | 0.042 | -0.06 | -0.018 | 18.69 |
[HEtHex][Butala]S4 | N34…H35—O58 | 0.073 | 0.086 | 0.047 | -0.073 | -0.026 | 22.87 |
[HEtHex][Butala]S5 | N34…H35—O58 | 0.076 | 0.083 | 0.049 | -0.077 | -0.028 | 24.19 |
[HEtHex][Hexala]S1 | N31…H33—O57 | 0.061 | 0.101 | 0.042 | -0.06 | -0.017 | 18.72 |
[HEtHex][Hexala]S2 | N31…H33—O58 | 0.065 | 0.098 | 0.044 | -0.064 | -0.02 | 20.06 |
[HEtHex][Hexala]S3 | N31…H32—O58 | 0.062 | 0.095 | 0.042 | -0.06 | -0.018 | 18.74 |
[HEtHex][Hexala]S4 | N34…H35—O57 | 0.070 | 0.090 | 0.046 | -0.069 | -0.023 | 21.70 |
[HEtHex][Hexala]S5 | N34…H35—O58 | 0.076 | 0.083 | 0.049 | -0.076 | -0.028 | 23.95 |
Bond | H???Y/ ? | X—H???Y/ ? | Bond angle/(°) | IR shift | EHB/ (kcal?mol-1) | Density ρc/a.u. | E(2)/ (kcal?mol-1) |
---|---|---|---|---|---|---|---|
strong H-bond | 1.2—1.5 | 2.2—2.5 | 170—180 | ? 25% | 15—40 | ? 0.05 | ? 36 |
H-bond for [HEtHex][Acylala] | 1.57—1.65 | 2.62—2.68 | 166—175 | 27%—37% | 18.69—24.19 | 0.061—0.076 | 43.58—57.58 |
Table 7 Criteria for strong H-bonds[29,30] and corresponding values for [HEtHex][Acylala]
Bond | H???Y/ ? | X—H???Y/ ? | Bond angle/(°) | IR shift | EHB/ (kcal?mol-1) | Density ρc/a.u. | E(2)/ (kcal?mol-1) |
---|---|---|---|---|---|---|---|
strong H-bond | 1.2—1.5 | 2.2—2.5 | 170—180 | ? 25% | 15—40 | ? 0.05 | ? 36 |
H-bond for [HEtHex][Acylala] | 1.57—1.65 | 2.62—2.68 | 166—175 | 27%—37% | 18.69—24.19 | 0.061—0.076 | 43.58—57.58 |
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