Host-Guest Complexations of Amine Boranes and Isoelectronic/Isostructural Quaternary Alkylammonium Cations by Cucurbit[7]uril in Aqueous Solution

<p>Structures of amine borane guests (R<sub>3</sub>NBH<sub>3</sub>) with the limiting chemical shift changes (<span class="nowrap"><svg height="12.4698pt" id="M51" style="vertical-align:-3.18147pt" version="1.1" viewbox="-0.0498162 -9.28833 27.8865 12.4698" width="27.8865pt" xmlns="http://www.w3.org/2000/svg"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M600 0V24L339 665L311 657L43 24V0H600ZM497 50H107L303 539L497 50Z"></path></g><g transform="matrix(.013,0,0,-0.013,8.364,0)"><path d="M494 514C482 587 419 712 303 712C238 712 174 667 174 603C174 561 205 514 249 449C219 438 187 422 162 407C93 366 23 283 23 177C23 69 87 -12 190 -12C244 -12 288 5 328 33C406 87 444 170 444 249C444 329 404 391 331 475C265 550 222 605 222 627C222 647 238 657 267 657C355 657 421 585 484 499L494 514ZM359 234C359 143 319 30 219 30C172 30 114 75 114 178C114 275 163 343 195 378C212 397 241 415 269 425C305 382 359 313 359 234Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,14.76,3.132)"><path d="M244 0V30C178 35 170 41 170 107V710C136 697 72 680 18 675V647C83 642 89 639 89 572V107C89 43 80 35 16 30V0H244Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,17.126,3.132)"><path d="M138 535C169 535 191 560 191 589C191 620 168 644 139 644S85 620 85 589C85 560 110 535 138 535ZM257 0V30C192 35 185 43 185 109V453C142 435 94 422 40 414V386C101 378 104 372 104 311V109C104 41 97 35 33 30V0H257Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,19.629,3.132)"><path d="M810 0V30C751 35 744 40 744 106V296C744 396 694 451 614 451C583 451 558 438 537 425C512 409 485 391 454 368C434 420 390 451 342 451C309 451 285 439 260 424C228 405 206 387 185 372V453C141 434 90 421 43 413V386C102 378 105 373 105 309V106C105 41 96 35 29 30V0H243V30C194 35 185 41 185 106V335C216 360 256 389 297 389C357 389 384 348 384 275V106C384 41 374 35 312 30V0H530V30C475 35 465 41 465 104V294C465 313 464 324 463 336C502 367 539 389 576 389C637 389 663 346 663 274V109C663 41 653 35 593 30V0H810Z"></path></g></svg>,</span> ppm) of the guest proton (C-H in black and B-H in red) and boron (blue) resonances upon complexation by CB<span class="nowrap"><svg height="11.439pt" id="M52" style="vertical-align:-2.15067pt" version="1.1" viewbox="-0.0498162 -9.28833 15.3667 11.439" width="15.3667pt" xmlns="http://www.w3.org/2000/svg"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M290 -163V-135C183 -126 181 -122 181 -44V583C181 662 184 666 290 675V703H120V-163H290Z"></path></g><g transform="matrix(.013,0,0,-0.013,4.485,0)"><path d="M447 623H65C61 580 56 530 47 475H76C100 541 106 550 172 550H388C308 376 196 170 91 -1L98 -12L172 -2C268 204 360 408 455 611L447 623Z"></path></g><g transform="matrix(.013,0,0,-0.013,10.727,0)"><path d="M226 -163V703H56V676C162 667 165 662 165 584V-43C165 -122 162 -126 56 -136V-163H226Z"></path></g></svg>.</span> The values in the square brackets are the <svg height="12.4698pt" id="M53" style="vertical-align:-3.18147pt" version="1.1" viewbox="-0.0498162 -9.28833 27.8865 12.4698" width="27.8865pt" xmlns="http://www.w3.org/2000/svg"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M600 0V24L339 665L311 657L43 24V0H600ZM497 50H107L303 539L497 50Z"></path></g><g transform="matrix(.013,0,0,-0.013,8.364,0)"><path d="M494 514C482 587 419 712 303 712C238 712 174 667 174 603C174 561 205 514 249 449C219 438 187 422 162 407C93 366 23 283 23 177C23 69 87 -12 190 -12C244 -12 288 5 328 33C406 87 444 170 444 249C444 329 404 391 331 475C265 550 222 605 222 627C222 647 238 657 267 657C355 657 421 585 484 499L494 514ZM359 234C359 143 319 30 219 30C172 30 114 75 114 178C114 275 163 343 195 378C212 397 241 415 269 425C305 382 359 313 359 234Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,14.76,3.132)"><path d="M244 0V30C178 35 170 41 170 107V710C136 697 72 680 18 675V647C83 642 89 639 89 572V107C89 43 80 35 16 30V0H244Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,17.126,3.132)"><path d="M138 535C169 535 191 560 191 589C191 620 168 644 139 644S85 620 85 589C85 560 110 535 138 535ZM257 0V30C192 35 185 43 185 109V453C142 435 94 422 40 414V386C101 378 104 372 104 311V109C104 41 97 35 33 30V0H257Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,19.629,3.132)"><path d="M810 0V30C751 35 744 40 744 106V296C744 396 694 451 614 451C583 451 558 438 537 425C512 409 485 391 454 368C434 420 390 451 342 451C309 451 285 439 260 424C228 405 206 387 185 372V453C141 434 90 421 43 413V386C102 378 105 373 105 309V106C105 41 96 35 29 30V0H243V30C194 35 185 41 185 106V335C216 360 256 389 297 389C357 389 384 348 384 275V106C384 41 374 35 312 30V0H530V30C475 35 465 41 465 104V294C465 313 464 324 463 336C502 367 539 389 576 389C637 389 663 346 663 274V109C663 41 653 35 593 30V0H810Z"></path></g></svg> values for the corresponding quaternary alkylammonium cations (R<sub>3</sub>NC<span class="nowrap"><svg height="14.0878pt" id="M54" style="vertical-align:-3.291101pt" version="1.1" viewbox="-0.0498162 -10.7967 21.1205 14.0878" width="21.1205pt" xmlns="http://www.w3.org/2000/svg"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M729 650H468V622C546 615 554 610 554 527V365H213V527C213 610 221 616 297 622V650H38V622C120 616 128 611 128 527V123C128 39 120 34 40 28V0H303V28C221 34 213 40 213 123V322H554V123C554 39 546 34 460 28V0H728V28C647 34 639 39 639 123V527C639 610 647 615 729 622V650Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,9.958,3.132)"><path d="M290 377C321 398 342 415 358 430C378 450 389 473 389 502C389 578 329 635 238 635H237C184 635 137 610 109 578L64 515L88 493C112 529 154 573 208 573S303 542 303 482C303 409 233 370 141 341L149 308C165 313 190 319 215 319C272 319 341 283 341 193C342 98 292 43 222 43C163 43 122 72 96 94C88 101 79 100 70 94C61 87 47 73 46 60C44 47 48 37 62 23C76 10 118 -12 165 -12C238 -12 430 62 430 223C430 297 379 359 290 375V377Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,14.942,-5.741)"><path d="M556 236V289H337V504H275V289H56V236H275V-4H337V236H556Z"></path></g></svg>).</span></p>

Heteroatom Chemistry

fig2

Figure 2

Figure 2: Host-Guest Complexations of Amine Boranes and Isoelectronic/Isostructural Quaternary Alkylammonium Cations by Cucurbit[7]uril in Aqueous Solution 

Figure 2 | Host-Guest Complexations of Amine Boranes and Isoelectronic/Isostructural Quaternary Alkylammonium Cations by Cucurbit[7]uril in Aqueous Solution 