6
I. Galkina et al. / Journal of Organometallic Chemistry 910 (2020) 121131
spectrum (D2O) dH, ppm (J/Hz): 2.57 (t, 2H, PeCH2eCH2, JHH 7.2),
3.20 (t, 2H, PeCH2eCH2, JHH 7.4), 5.52 (s, 1H, PeCH), 7.56e7.78 (m,
10H, Ph2P). 13C NMR spectrum (D2O), dC, ppm, 100,6 MHz: 16.93 (d,
PeCH2, 1JPC 51.8), 36.65 (s, PeCH2eCH2), 69.0 (d, PeCH, 1JPC 61.3),
115.23 (d, Cipso, 1JPC 86.2), 129.77 (d, Co, 2JPC 23.1), 133.65 (d, Cm, 3JPC
8.7), 133.49 (d, Cm, 3JPC 8.7), 134.76 (d, Cp, 4JPC 21.3), 176.36 (d, C(O)O,
2JPC 17.5). 31P NMR spectrum (D2O): dP 27.48 ppm. Elemental
analysis: C34H36O6P2. Found, %: C 67.93, H 6.84, P 10.89. Calculated,
%: C 67.77, H 6.02, P 10.28.
4
2
14.0), 135.00 (d, Cp, JPC 13.7), 169.7 (d, C(O)O, JPC 17.5). 31P NMR
spectrum (D2O): dP 27.3 ppm. Elemental analysis: C17H17O5P. Found,
%: C 61.55, H 5.11, P 9.23. Calculated, %: C 61.44, H 5.15, P 9.32.
Declaration of competing interest
The authors declare that they have no known competing
financial interests or personal relationships that could have
appeared to influence the work reported in this paper.
4.2.4. 2,2’-(methylenebis(diphenylphosphonionediyl))bis(2-
hydroxyacetate) 4
Carboxylate phosphabetaine 4 was synthesized on the basis of
1,1-bis(diphenylphosphino)methane. Yield 75%. Colorless crystals
Acknowledgement
with m.p.100e102 ꢁC, soluble in water and chloroform. IR ( /cmꢀ1):
n
This work was funded by the subsidy allocated to Kazan Federal
997, 1116, 1181, 1338, 1435, 1621, 1716, 3055. 1H NMR spectrum
(D2O) dH, ppm (J/Hz): 1.96 (d, 2H, Pe CH2, JHH 10.6), 5.19 (s, 2H,
PeCH), 7.36e7.51 (m, 20H, Ph2P). 13C NMR spectrum (D2O), dC, ppm,
University for the state assignment in the sphere of scientific ac-
ꢁ
tivities (N . 4.5888.2017/8.9).
1
1
100,6 MHz: 18.91 (d, PeCH2, JPC 50.8), 69.0 (d, PeCH, JPC 61.3),
References
114.33 (d, Cipso, 1JPC 83.2), 130.77 (d, Co, 2JPC 24.1), 133.45 (d, Cm, 3JPC
14.2), 135.23 (d, Cp, JPC 13.5), 168.7 (d, C(O)O, JPC 14.5). 31P NMR
spectrum (D2O): dP 40.51 ppm. Elemental analysis: C29H26O6P.
Found, %: C 69.55, H 5.49, P 6.86. Calculated, %: C 69.45, H 5.23, P
6.18.
4
2
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n
901, 997, 1109, 1344, 1438, 1633, 1731, 3064. 1H NMR spectrum
(D2O) dH, ppm (J/Hz): 3.08 (s, 4H, P-(CH2)2), 5.18 (s, 2H, PeCH),
7.49e7.82 (m, 20H, Ph2P). 13C NMR spectrum (D2O), dC, ppm,
1
100,6 MHz: 21.53 (d, PeCH2, 1JPC 65.9), 85.99 (s, Pe CH JPC 54.0),
116.72 (d, Cipso, 1JPC 84.2), 130.03 (d, Co, 2JPC 12.8), 133.53 (d, Cm, 3JPC
4
2
4.4), 135.41 (d, Cp, JPC 7.3), 170.7 (d, C(O)O, JPC 19.5). 31P NMR
spectrum (D2O): dP 28.08 ppm. Elemental analysis: C30H28O6P2.
Found, %: C 65.79, H 5.11, P 11.24. Calculated, %: C 65.93, H 5.16, P
11.34.
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4.2.6. 2,2’-(propane-1,3-diylbis(diphenylphosphonionediyl))bis(2-
hydroxyacetate) 6
Carboxylate phosphabetaine 6 was synthesized on the basis of
1,3-bis(diphenylphosphino)propane. Yield 77%. Colorless crystals
with m.p. 112e116 ꢁC, soluble in water and chloroform. IR ( /cmꢀ1):
n
896, 969, 997, 1111, 1341, 1437, 1637, 3060. 1H NMR spectrum (D2O)
dH, ppm (J/Hz): 1.47 (d, 2H, PeCH2eCH2 JHH 6.3), 2.97 (s, 4H,
PeCH2), 5.35 (s, 2H, PeCH), 7.49e7.82 (m, 20H, Ph2P). 13C NMR
1
spectrum (D2O), dC, ppm, 100,6 MHz: 15.84 (d, PeCH2, JPC 56.2),
2
21.31 (d, PeCH2eCH2, JPC 48.2), 68.32 (d, PeCH, 1JPC 59.0), 115.89
2
3
(d, Cipso, 1JPC 86.3), 129.77 (d, Co, JPC 24.5), 133.32 (d, Cm, JPC 6.0),
135.00 (d, Cp, JPC 13.5), 170.20 (d, C(O)O, JPC 17.5). 31P NMR spec-
trum (D2O): dP 26.74 ppm. Elemental analysis: C31H30O6P2. Found,
%: C 66.79, H 5.11, P 11.24. Calculated, %: C 66.43, H 5.39, P 11.05.
4
2
4.2.7. 2,2’-(hexane-1,6-diylbis(diphenylphosphonionediyl))bis(2-
hydroxyacetate) 7
Carboxylate phosphabetaine 7 was synthesized on the basis of
1,6-bis(diphenylphosphino)hexane. Yield 85%. Colorless crystals
with m.p. 77e80 ꢁC, soluble in water and chloroform. IR ( /cmꢀ1):
n
918, 981, 1027, 1119, 1179, 1436, 1633, 2937. 1H NMR spectrum (D2O)
dH, ppm (J/Hz): 1.21 (d, 8H, PeCH2-(CH2)4), JHH 13.5), 2.74 (d, 4H,
PeCH2), JHH 13.5), 7.44e7.79 (m, 20H, Ph2P). 13C NMR spectrum
1
(D2O), dC, ppm, 100,6 MHz: 16.63 (s, PeCH2 JPC 56.4), 20.31 (d,
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with unsaturated carboxylic acids and their derivatives, Heteroat. Chem. 17
2
3
PeCH2eCH2, JPC 48.0), 28.27 (d, PeCH2eCH2-(CH2)2 JPC 15.1),
68.07 (d, PeCH, 1JPC 58.4), 117.5 (d, Cipso, 1JPC 84.3), 129.72 (d, Co, 2JPC