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. 2012 Aug 31;8:1406–1442. doi: 10.3762/bjoc.8.163

Table 9.

BHCA values of Lewis base, ordered by increasing BHCA values.

system BHCA [kJ/mol] system BHCA [kJ/mol]

PH3 (343) +77.8 NH3 (344) +84.3
Ph2P–NEt2 (251) +137.7a Inline graphic
(345)
+148.1b
NEt3 (45) +150.7 NMe3 (20) +153.0
Inline graphic
(346)
+157.8b pyridine (1) +160.0
Inline graphic
(347)
+164.4b Inline graphic
(44)
+167.8
Inline graphic
(14)
+171.7 Inline graphic
(53)
+184.6
Inline graphic
(24)
+186.4c P(OPh)3 (252) +193.0
Inline graphic
(348)
+200.5b Inline graphic
(254)
+207.7
P(OEt)3 (255) +208.1 Inline graphic
(54)
+213.0b
PMe3 (70) +215.5 Inline graphic
(56)
+221.4b
P(iPr)3 (117) +224.8 Inline graphic
(349)
+225.8b
PPhMe2 (256) +230.1 PPh(iPr)2 (279) +230.4
PEt3 (98) +230.6 PPh2t-Bu (281) +232.7
Inline graphic
(350)
+233.3b Inline graphic
(57)
+233.3b
PPh3 (89) +235.0 PPh2Me (259) +236.0
PPhEt2 (261) +237.6 PPh2Et (264) +241.1
PPh2c-Pr (267) +241.9 Inline graphic
(294)
+242.1
PPh2n-Bu (102) +243.2 PPhn-Pr2 (269) +244.0
PPh2n-Pr (270) +245.8 Ph2P–NEt2 (251) +245.8d
Inline graphic
(276)
+246.0 PPhn-Bu2 (280) +248.0
PPh2c-Bu (278) +248.3 PPh2(iPr) (268) +248.3
Pc-Hex3 (124) +249.8 PPh2c-Hex (285) +250.5
Inline graphic
(60)
+250.6e PPh2c-Pen (286) +251.3
Inline graphic
(295)
+252.4 PPh2c-Hep (289) +254.5
Inline graphic
(298)
+266.5 Inline graphic
(300)
+306.2

aBHCA value on nitrogen; bpyridine nitrogen; cN3; dBHCA value on phosphorus; eN(sp2).